EP3363288A1 - Composition for destruction of microalgae or sphaerocarpus - Google Patents
Composition for destruction of microalgae or sphaerocarpus Download PDFInfo
- Publication number
- EP3363288A1 EP3363288A1 EP16855619.9A EP16855619A EP3363288A1 EP 3363288 A1 EP3363288 A1 EP 3363288A1 EP 16855619 A EP16855619 A EP 16855619A EP 3363288 A1 EP3363288 A1 EP 3363288A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- genus
- substituted
- composition
- formulae
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 160
- 230000006378 damage Effects 0.000 title abstract description 13
- 241000195940 Bryophyta Species 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 22
- 241000195493 Cryptophyta Species 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 14
- 241000206758 Heterosigma Species 0.000 claims description 13
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
- 125000006753 (C1-C60) heteroaryl group Chemical group 0.000 claims description 9
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 8
- 239000003225 biodiesel Substances 0.000 claims description 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 241000192700 Cyanobacteria Species 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 241000206761 Bacillariophyta Species 0.000 claims description 6
- 241000199914 Dinophyceae Species 0.000 claims description 6
- 241000192701 Microcystis Species 0.000 claims description 6
- 241000195628 Chlorophyta Species 0.000 claims description 5
- 241001300810 Cochlodinium Species 0.000 claims description 5
- 241000200146 Heterocapsa Species 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 241000200031 Alexandrium Species 0.000 claims description 4
- 241000200138 Ceratium Species 0.000 claims description 4
- 241000180097 Chattonella Species 0.000 claims description 4
- 241000218612 Dinophysis Species 0.000 claims description 4
- 241000200106 Emiliania Species 0.000 claims description 4
- 241000195623 Euglenida Species 0.000 claims description 4
- 241001245610 Eutreptiella Species 0.000 claims description 4
- 241000200287 Gymnodinium Species 0.000 claims description 4
- 241000200174 Noctiluca Species 0.000 claims description 4
- 241001232546 Pfiesteria Species 0.000 claims description 4
- 241000200248 Prorocentrum Species 0.000 claims description 4
- 241001518925 Raphidophyceae Species 0.000 claims description 4
- 241000534670 Scrippsiella Species 0.000 claims description 4
- 241000206764 Xanthophyceae Species 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 241000192542 Anabaena Species 0.000 claims description 2
- 241000183405 Andreaeobryopsida Species 0.000 claims description 2
- 241000183392 Andreaeopsida Species 0.000 claims description 2
- 241000192660 Aphanizomenon Species 0.000 claims description 2
- 241001491696 Asterionella Species 0.000 claims description 2
- 241001536324 Botryococcus Species 0.000 claims description 2
- 241000195876 Bryopsida Species 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 241000227752 Chaetoceros Species 0.000 claims description 2
- 241001478806 Closterium Species 0.000 claims description 2
- 241001147476 Cyclotella Species 0.000 claims description 2
- 241000206743 Cylindrotheca Species 0.000 claims description 2
- 241000195634 Dunaliella Species 0.000 claims description 2
- 241000227697 Eucampia Species 0.000 claims description 2
- 241000195620 Euglena Species 0.000 claims description 2
- 241000364669 Leptocylindrus Species 0.000 claims description 2
- 241001491711 Melosira Species 0.000 claims description 2
- 241000180701 Nitzschia <flatworm> Species 0.000 claims description 2
- 241000326556 Odontella <springtail> Species 0.000 claims description 2
- 241000622389 Oedipodiopsida Species 0.000 claims description 2
- 241000192497 Oscillatoria Species 0.000 claims description 2
- 241000196152 Pediastrum Species 0.000 claims description 2
- 241000199911 Peridinium Species 0.000 claims description 2
- 241000183390 Polytrichopsida Species 0.000 claims description 2
- 241000195663 Scenedesmus Species 0.000 claims description 2
- 241000206732 Skeletonema costatum Species 0.000 claims description 2
- 241000183391 Sphagnopsida Species 0.000 claims description 2
- 241001426193 Synedra Species 0.000 claims description 2
- 241000183407 Takakiopsida Species 0.000 claims description 2
- 241000622385 Tetraphidopsida Species 0.000 claims description 2
- 241001491691 Thalassiosira Species 0.000 claims description 2
- 241000383524 Trachelomonas Species 0.000 claims description 2
- 241000391106 Uroglena Species 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 abstract description 5
- 230000012010 growth Effects 0.000 abstract description 2
- 230000003405 preventing effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 128
- 238000006243 chemical reaction Methods 0.000 description 95
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 90
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 88
- 239000007795 chemical reaction product Substances 0.000 description 47
- 238000005160 1H NMR spectroscopy Methods 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- 239000000741 silica gel Substances 0.000 description 45
- 229910002027 silica gel Inorganic materials 0.000 description 45
- 238000004809 thin layer chromatography Methods 0.000 description 45
- 239000012046 mixed solvent Substances 0.000 description 44
- 238000003786 synthesis reaction Methods 0.000 description 44
- 230000002829 reductive effect Effects 0.000 description 43
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 42
- 239000000284 extract Substances 0.000 description 42
- 239000007788 liquid Substances 0.000 description 40
- 229910000033 sodium borohydride Inorganic materials 0.000 description 37
- 239000012279 sodium borohydride Substances 0.000 description 37
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- -1 feed Substances 0.000 description 13
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 241000252212 Danio rerio Species 0.000 description 11
- 230000002353 algacidal effect Effects 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- 241000295556 Chattonella marina Species 0.000 description 9
- 241001300495 Cochlodinium polykrikoides Species 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 0 CC1=CC1N* Chemical compound CC1=CC1N* 0.000 description 8
- 241000206757 Heterosigma akashiwo Species 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 6
- 241000251468 Actinopterygii Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 241001494246 Daphnia magna Species 0.000 description 5
- 241000192710 Microcystis aeruginosa Species 0.000 description 5
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 5
- 238000011047 acute toxicity test Methods 0.000 description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- AJCAMRFVASYHTQ-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCNCC1=CC=C(Cl)C(Cl)=C1 AJCAMRFVASYHTQ-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 239000013505 freshwater Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 230000000050 nutritive effect Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BQHVIMLXURNCBU-UHFFFAOYSA-N 3,4-dichloro-n-[2-(diethylamino)ethyl]benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(Cl)C(Cl)=C1 BQHVIMLXURNCBU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000007667 floating Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000001000 micrograph Methods 0.000 description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 3
- XUDVOLHLDGBFEQ-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-1-pyridin-4-ylmethanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCC1=CC=NC=C1 XUDVOLHLDGBFEQ-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000013535 sea water Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- DJSKSKCQEQMUQF-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-(pyridin-2-ylmethyl)methanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCC1=CC=CC=N1 DJSKSKCQEQMUQF-UHFFFAOYSA-N 0.000 description 2
- HVVCLQYSDJBBES-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-(pyridin-3-ylmethyl)methanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCC1=CC=CN=C1 HVVCLQYSDJBBES-UHFFFAOYSA-N 0.000 description 2
- JGFFGEWFUWVQEE-UHFFFAOYSA-N 2-[(2-pyridin-2-ylethylamino)methyl]phenol Chemical compound OC1=CC=CC=C1CNCCC1=CC=CC=N1 JGFFGEWFUWVQEE-UHFFFAOYSA-N 0.000 description 2
- ZOUNDIYZTMAZBA-UHFFFAOYSA-N 2-[3-[(3,4-dichlorophenyl)methylamino]propyl-(2-hydroxyethyl)amino]ethanol Chemical compound ClC=1C=C(CNCCCN(CCO)CCO)C=CC=1Cl ZOUNDIYZTMAZBA-UHFFFAOYSA-N 0.000 description 2
- HLKMRULDBKAOAB-UHFFFAOYSA-N 3,4-dichloro-n-[2-(dimethylamino)ethyl]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(Cl)C(Cl)=C1 HLKMRULDBKAOAB-UHFFFAOYSA-N 0.000 description 2
- RGPMSIDNUVIROO-UHFFFAOYSA-N 3,4-dichloro-n-[3-(diethylamino)propyl]benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC=C(Cl)C(Cl)=C1 RGPMSIDNUVIROO-UHFFFAOYSA-N 0.000 description 2
- JLHTYEQWOKFUFM-UHFFFAOYSA-N 3,4-dichloro-n-[3-(dimethylamino)propyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(Cl)C(Cl)=C1 JLHTYEQWOKFUFM-UHFFFAOYSA-N 0.000 description 2
- QDWHHNQJNXGPRJ-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)propan-1-amine Chemical compound NCCCC1=CC=C(Cl)C(Cl)=C1 QDWHHNQJNXGPRJ-UHFFFAOYSA-N 0.000 description 2
- DFORBMFOFAEZHP-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)butan-1-amine Chemical compound NCCCCC1=CC=C(Cl)C(Cl)=C1 DFORBMFOFAEZHP-UHFFFAOYSA-N 0.000 description 2
- QSBCYYUOBHLQLH-UHFFFAOYSA-N 4-bromo-n-[(3,4-dichlorophenyl)methyl]aniline Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1=CC=C(Br)C=C1 QSBCYYUOBHLQLH-UHFFFAOYSA-N 0.000 description 2
- VIZWDAOZENFBIZ-UHFFFAOYSA-N 4-chloro-n-[(3,4-dichlorophenyl)methyl]aniline Chemical compound C1=CC(Cl)=CC=C1NCC1=CC=C(Cl)C(Cl)=C1 VIZWDAOZENFBIZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QGLSJLWMBSGWDT-UHFFFAOYSA-N N',N'-dibutyl-N-[(3,4-dichlorophenyl)methyl]ethane-1,2-diamine Chemical compound C(CCC)N(CCNCC1=CC(=C(C=C1)Cl)Cl)CCCC QGLSJLWMBSGWDT-UHFFFAOYSA-N 0.000 description 2
- KYTQEMYMRAWOEX-UHFFFAOYSA-N N-[(3,4-dichlorophenyl)methyl]-4,4-dimethoxybutan-1-amine Chemical compound ClC=1C=C(CNCCCC(OC)OC)C=CC=1Cl KYTQEMYMRAWOEX-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- MJDIGRUBXWNCPF-UHFFFAOYSA-N n',n'-dibutyl-n-[(3,4-dichlorophenyl)methyl]propane-1,3-diamine Chemical compound CCCCN(CCCC)CCCNCC1=CC=C(Cl)C(Cl)=C1 MJDIGRUBXWNCPF-UHFFFAOYSA-N 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- BKCIQULLXLXXEE-UHFFFAOYSA-N n-[(2-bromophenyl)methyl]-2-pyridin-2-ylethanamine Chemical compound BrC1=CC=CC=C1CNCCC1=CC=CC=N1 BKCIQULLXLXXEE-UHFFFAOYSA-N 0.000 description 2
- FPWAPECSISWNRW-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-1-phenylmethanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCC1=CC=CC=C1 FPWAPECSISWNRW-UHFFFAOYSA-N 0.000 description 2
- ARVSOTMCJFJKOF-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2,3-dihydro-1h-inden-1-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1C2=CC=CC=C2CC1 ARVSOTMCJFJKOF-UHFFFAOYSA-N 0.000 description 2
- SKZLXAQIIJTTGL-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-phenylethanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCCC1=CC=CC=C1 SKZLXAQIIJTTGL-UHFFFAOYSA-N 0.000 description 2
- HZBXJWMVHPPPFH-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-pyridin-2-ylethanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCCC1=CC=CC=N1 HZBXJWMVHPPPFH-UHFFFAOYSA-N 0.000 description 2
- OYCXCUMBRLPLIH-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-pyridin-3-ylethanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCCC1=CC=CN=C1 OYCXCUMBRLPLIH-UHFFFAOYSA-N 0.000 description 2
- DZELVMLZXCQKHH-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-pyridin-4-ylethanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNCCC1=CC=NC=C1 DZELVMLZXCQKHH-UHFFFAOYSA-N 0.000 description 2
- MGPARZLCQFPJOU-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-3-methylbutan-1-amine Chemical compound CC(C)CCNCC1=CC=C(Cl)C(Cl)=C1 MGPARZLCQFPJOU-UHFFFAOYSA-N 0.000 description 2
- VFNXYZKGLYTZOK-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-4-fluoroaniline Chemical compound C1=CC(F)=CC=C1NCC1=CC=C(Cl)C(Cl)=C1 VFNXYZKGLYTZOK-UHFFFAOYSA-N 0.000 description 2
- NNLSWOKOLBTIRH-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNCC1=CC=C(Cl)C(Cl)=C1 NNLSWOKOLBTIRH-UHFFFAOYSA-N 0.000 description 2
- NYSHFAAKOUWIBE-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNCC1=CC=C(Cl)C(Cl)=C1 NYSHFAAKOUWIBE-UHFFFAOYSA-N 0.000 description 2
- FIGFDBVBDYLQFP-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCNCC1=CC=C(Cl)C(Cl)=C1 FIGFDBVBDYLQFP-UHFFFAOYSA-N 0.000 description 2
- DNLJKKQHJDOTLP-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]aniline Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1=CC=CC=C1 DNLJKKQHJDOTLP-UHFFFAOYSA-N 0.000 description 2
- YVZJVLADBODSAQ-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]butan-1-amine Chemical compound CCCCNCC1=CC=C(Cl)C(Cl)=C1 YVZJVLADBODSAQ-UHFFFAOYSA-N 0.000 description 2
- UXPVUUPBCOTHNO-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]cyclobutanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1CCC1 UXPVUUPBCOTHNO-UHFFFAOYSA-N 0.000 description 2
- GYAUOGWEDNRKHG-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]cycloheptanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1CCCCCC1 GYAUOGWEDNRKHG-UHFFFAOYSA-N 0.000 description 2
- PEZCMQDKHGXWKH-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]cyclohexanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1CCCCC1 PEZCMQDKHGXWKH-UHFFFAOYSA-N 0.000 description 2
- IDLXFTKZQGLOPK-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]cyclooctanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1CCCCCCC1 IDLXFTKZQGLOPK-UHFFFAOYSA-N 0.000 description 2
- QBEWAWCVBHNCPZ-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]cyclopentanamine Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC1CCCC1 QBEWAWCVBHNCPZ-UHFFFAOYSA-N 0.000 description 2
- SHYHRKGWPUZGJW-UHFFFAOYSA-N n-[(3-bromophenyl)methyl]-2-pyridin-2-ylethanamine Chemical compound BrC1=CC=CC(CNCCC=2N=CC=CC=2)=C1 SHYHRKGWPUZGJW-UHFFFAOYSA-N 0.000 description 2
- HXOZUVSBDKCGAI-UHFFFAOYSA-N n-[(4-bromophenyl)methyl]-2-pyridin-2-ylethanamine Chemical compound C1=CC(Br)=CC=C1CNCCC1=CC=CC=N1 HXOZUVSBDKCGAI-UHFFFAOYSA-N 0.000 description 2
- WUDUNBALAGWKQB-UHFFFAOYSA-N n-benzyl-2-pyridin-2-ylethanamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=N1 WUDUNBALAGWKQB-UHFFFAOYSA-N 0.000 description 2
- KARSJEQFQOBUHO-UHFFFAOYSA-N n-benzylcycloheptanamine Chemical compound C=1C=CC=CC=1CNC1CCCCCC1 KARSJEQFQOBUHO-UHFFFAOYSA-N 0.000 description 2
- IYWYMFZAZUYNLC-UHFFFAOYSA-N n-benzylcyclohexanamine Chemical compound C=1C=CC=CC=1CNC1CCCCC1 IYWYMFZAZUYNLC-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 231100000719 pollutant Toxicity 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical class NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 1
- FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- KPRZOPQOBJRYSW-UHFFFAOYSA-N 2-(aminomethyl)phenol Chemical class NCC1=CC=CC=C1O KPRZOPQOBJRYSW-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- FKJVYOFPTRGCSP-UHFFFAOYSA-N 2-[3-aminopropyl(2-hydroxyethyl)amino]ethanol Chemical compound NCCCN(CCO)CCO FKJVYOFPTRGCSP-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- DXCXWVLIDGPHEA-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-[(4-ethylpiperazin-1-yl)methyl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCN(CC1)CC DXCXWVLIDGPHEA-UHFFFAOYSA-N 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- NAHHNSMHYCLMON-UHFFFAOYSA-N 2-pyridin-3-ylethanamine Chemical compound NCCC1=CC=CN=C1 NAHHNSMHYCLMON-UHFFFAOYSA-N 0.000 description 1
- IDLHTECVNDEOIY-UHFFFAOYSA-N 2-pyridin-4-ylethanamine Chemical compound NCCC1=CC=NC=C1 IDLHTECVNDEOIY-UHFFFAOYSA-N 0.000 description 1
- XURBWYCGQQXTHJ-UHFFFAOYSA-N 3,4-dichlorobenzamide Chemical class NC(=O)C1=CC=C(Cl)C(Cl)=C1 XURBWYCGQQXTHJ-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- TYVAXMOICMBSMT-UHFFFAOYSA-N 4,4-dimethoxybutan-1-amine Chemical compound COC(OC)CCCN TYVAXMOICMBSMT-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000238571 Cladocera Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 241000993432 Heterocapsa circularisquama Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 210000002816 gill Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229960000829 kaolin Drugs 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PWNDYKKNXVKQJO-UHFFFAOYSA-N n',n'-dibutylethane-1,2-diamine Chemical compound CCCCN(CCN)CCCC PWNDYKKNXVKQJO-UHFFFAOYSA-N 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- JJMCCHQJHLDLGI-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-methoxyethanamine Chemical compound COCCNCC1=CC=C(Cl)C(Cl)=C1 JJMCCHQJHLDLGI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000008239 natural water Substances 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229940080314 sodium bentonite Drugs 0.000 description 1
- 229910000280 sodium bentonite Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229940032158 sodium silicate Drugs 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/40—Devices for separating or removing fatty or oily substances or similar floating material
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
Definitions
- the present disclosure relates to a composition for destruction of microalgae or mosses.
- Microalgae as photosynthetic aquatic unicellular organisms are commonly referred to as phytoplankton.
- Microalgae may be used for wastewater treatment, immobilization of carbon dioxide, and the like, due to their diverse abilities, and have been used for production of useful materials such as fuel materials, cosmetics, feed, food coloring materials, and medicinal raw materials, while their fields of application have been widened due to the continuous discovery of useful value-added materials from microalgae.
- Microalgae as a biological resource which is free of the criticism on the use of food resources for energy production, may generate biofuels having similar physical properties to petroleum diesel.
- An energy conversion process for producing biodiesel from microalgae involves production and harvest of microalgae biomass, a process of oil extraction from the microalgae biomass, and a transesterification reaction of the extracted oil.
- the process of oil extraction from microalgae which is controversial due to its high cost, is regarded as a bottleneck in high lipid productivity and biodiesel production. Accordingly, an efficient oil extraction apparatus and method are required prior to the production of biodiesel from microalgae.
- microalgae also include harmful algae which result in abnormal proliferation of algae such as that of a green tide or red tide phenomenon.
- Green tide refers to a phenomenon in which the color of water turns into a prominent green color due to overproliferation and aggregation of floating algae, i.e., phytoplankton, on the water surface of a eutrophic lake or a river with a slow stream.
- this green tide occurs only in freshwater, and may be caused by the inflow of various land pollutants such as industrial wastewater, domestic sewage, fertilizers, pesticides, and livestock and human manure, into a river or lake, wherein these pollutants are deposited in the lower portion of the body of water and decomposed by bacteria into organic matter, which then generates nitrogen and phosphorus which is fed on by plankton, thus causing green tide in seawater and fresh water.
- Such green tide may reduce dissolved oxygen in water, and generate toxic algae and various green plankton, killing fish and aquatic organisms.
- heavy metals deposited at the bottom of the waters may flow in the waters to thereby contaminate fresh water and poison fish, further causing other problems such as environmental destruction and damage to natural aesthetics.
- Organisms that cause green tide are green algae, diatoms, blue-green algae, and phytomastigophora. Of these organisms, blue-green algae are the main cause of green tide.
- red tide refers to a phenomenon in which the color of seawater turns red, reddish brown, tan, green, yellow-green, or yellow due to abnormal proliferation of plankton caused by massive inflows of organic contaminants, nitrogen, phosphorus, and the like from land. Organisms which cause such red tide are mainly flagellates and diatoms.
- Such green tide and red tide caused by harmful algae may rapidly lead to an oxygen-deficient condition in the sea, due to the depletion of dissolved oxygen in the water, which consequently results in the mass death of fish and shellfish.
- Overproliferated plankton may adhere to the gills of fish such as to choke the fish.
- Flagellates such as Cochlodinium may generate harmful toxins which kill fish.
- about 50% of animal proteins consumed by about two billion of the world's population are supplied from the sea. Accordingly, the destruction of marine ecosystems by red tide may have a serious impact on such food resources, deteriorating the utility value of waters, and further raising more serious environmental issues beyond economic values.
- microalgae may not only generate bioenergy but may also mitigate harmful environmental problems.
- an oil extraction process for destruction of the cell membranes of microalgae to increase yield of extracted intracellular lipids.
- Typical oil extraction methods used so far are a solvent extraction method ( Chiara Samori et al., Bioresource Technology, 101:3274, 2010 ), a Soxhlet extraction method ( Ayhan Demirbas a and M.
- mosses For mosses, various nitrogen compounds may be generated from dead mosses, and mass proliferation of mosses may also cause green tide.
- Mosses may adhere to glass or walls, causing aesthetic unpleasantness in an aquarium, an exhibition hall, and the like, while deteriorating the water quality and functionality of a household water tank or industrial facilities such as a large water tank, a water storage tank, or an aquafarm. Therefore, it is also necessary to manage mosses in order to prevent and eliminate mosses.
- a benzylamine compound, a benzamide compound, and/or a phenyl propenone compound, each having a specific substituent may have an effect of destroying the cell membranes of microalgae, thus completing the present invention.
- the present disclose provides a composition for destroying microalgae or mosses, and a method of destroying microalgae or mosses by using the composition, wherein the composition includes a benzyl amine compound, a benzamide compound, and/or a phenyl propenone compound, each having a microalgae or mosses destruction effect.
- compositions for destroying microalgae or mosses wherein the composition includes a compound represented by one of Formulae 1 to 3 or a salt thereof as an active ingredient.
- a method of destroying microalgae or mosses including treating a moss cultivation facility, a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur, with the above-described composition for destroying microalgae or mosses.
- the term “area” may refer to a region under the environment where green tide or red tide likely occurs, including any aquatic environments including both seawater and fresh water.
- the term “treating” or “treatment” may refer to contacting microalgae or mosses with the composition according to one or more embodiments, and may include adding the composition according to one or more embodiments to water including the microalgae or mosses such as to make the composition contact the composition.
- the adding of the composition may include spraying the composition onto the water surface, or a stirring step, which may optionally be performed while moving over the water surface.
- the method may use an out-of-water treatment method.
- out-of-water treatment method may refer to drawing water from a water system, treating the water with the composition for destroying microalgae or mosses to remove the microalgae or mosses, and then discharging treated water back into the water system.
- water system may refer to a water supply source, for example, natural water systems such as water reservoirs, lakes, rivers, and the like, and artificial water systems such as aquafarms, fishing spots, cultivation facilities, water zone in golf courses, water storage tanks, and the like.
- the method may include: drawing raw water including microalgae or mosses from a water system; treating the raw water with the composition according to one or more embodiments; and discharging treated water back into the water system.
- the method according to one or more embodiments may further include removing the remaining composition, the remaining microalgae or mosses, organic material, nutritive salts, and dead microalgae or mosses.
- the removing step may include a physical method such as precipitation, solid-liquid separation, or simple filtration, or a chemical method using copper sulfate, a chlorine-based material, ultraviolet rays, ozone, or the like.
- the method according to one or more embodiments may further include, before the treatment with the composition according to one or more embodiments, treating raw water with a flocculant to flocculate the algae .
- the resulting aggregate produced by the flocculant may be removed by floating it using air bubbles or by precipitation, and then the water (supernatant) from which the aggregate has been removed may be treated with the composition according to one or more embodiments, which may have advantages in terms of cost, since a lower amount of the composition may be used, and prevention of side effects which may likely occur from release of a high concentration of the composition.
- flocculant examples may be aluminum sulfate, ferric sulfate, ferric chloride, polyaluminum chloride, polyaluminum silicate sulfate, polyhydroxy aluminum silicate chloride, or polyamines.
- An auxiliary flocculant for example, sodium alginate, sodium silicate, bentonite, or kaolin, may be used.
- an acidic or alkaline pH adjuster may be used.
- the method according to one or more embodiments may use an in-water treatment method.
- in-water treatment method may refer to removing microalgae or mosses by spraying the composition according to one or more embodiments into a water system. Since the composition according to one or more embodiments is less toxic to other living organisms than to algae, the composition may be sprayed in an appropriate concentration range such as to treat the microalgae or mosses.
- the concentration of the composition may be appropriately adjusted according to a type of a water system to be treated, a pH, a salt concentration, a temperature, a composition, an area, a depth, a use, or aquatic organic distribution of the water system, types of microalgae or mosses to be treated, a concentration or distribution of the microalgae or mosses, a purpose of destruction of microalgae or mosses, a targeted achievement from the destruction, or the like.
- the “in-water treatment method” may further include removing the remaining composition, the remaining microalgae or mosses, organic material, nutritive salts, and dead microalgae or mosses.
- the removing step may include physical filtration using a filter such as filter paper, or may include floating the remaining materials as described above by spraying a flocculant at the same time as or sequently so as to remove the remaining materials.
- the removing step may include generating air bubbles to supply oxygen to water, increase efficiency, and allow the flocculation to float without settling.
- the composition according to one or more embodiments may be used to prevent green tide or red tide caused from microalgae or mosses.
- the amount of the composition may be further reduced.
- dead microalgae or mosses may function as nutritive salts contributing to the occurrence of green tide or red tide. Accordingly, together with) the in-water or out-of-water treatment method, a physical filtration, chemical treatment, or air bubble generation step may be further included.
- a moss cultivation facility a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur is treated with the composition for destroying microalgae or mosses, according to the one or more embodiments, growth and proliferation of microalgae may be inhibited, and damage from red tide and/or green tide may be prevented.
- a composition for destroying microalgae or mosses includes a compound represented by one of Formulae 1 to 3 or a salt thereof as an active ingredient:
- a 1 to A 3 may each independently be selected from hydrogen, deuterium, -N(R 11 )(R 12 ), a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubsti
- R 11 and R 12 may each independently be selected from hydrogen, deuterium, -F, - Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, and a substituted or unsubstituted C 1 -C 10 alkoxy group.
- a 1 to A 3 may each independently be selected from -N(R 11 )(R 12 ), a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 10 aryl group, and a substituted or unsubstituted C 1 -C 10 heteroaryl group.
- embodiments are not limited thereto.
- a 1 to A 3 may each independently be selected from groups represented by Formulae 4-1 to 4-16. However, embodiments are not limited thereto:
- * is a binding site to a neighboring atom.
- R 11 to R 14 , and R 21 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, and a substituted or unsubstituted C 1 -C 10 alkyl group.
- R 11 to R 14 may each independently be selected from a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group; and a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each substituted with -OH group, and R 21 may be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and -OH.
- b11 may be an integer of 0 to 2
- b12 may be an integer of 0 to 3
- b13 may be an integer of 0 to 4
- b14 may be an integer of 0 to 5
- b15 may be an integer of 0 to 6
- b16 may be an integer of 0 to 7, wherein b11 indicates the number of R 21 s.
- b11 indicates the number of R 21 s.
- at least two of R 21 s may be the same or differ from each other.
- the meanings of b12 to b16 may also be understood based on the description of b11 and the structures of Formula 4-1 to 4-16.
- b11 to b16 may each independently be 0 or 1.
- a 1 to A 3 may each independently be selected from groups represented by Formulae 5-1 to 5-23. However, embodiments are not limited thereto:
- * is a binding site to a neighboring atom.
- R 1 to R 3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, and a substituted or unsubstituted C 1 -C 10 alkoxy group.
- R 1 to R 3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, and a substituted or unsubstituted C 1 -C 10 alkyl group.
- embodiments are not limited thereto.
- R 1 to R 3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and -OH.
- b1 to b3 may each independently be an integer of 0 to 5.
- at least two of R 1 s may be the same or differ from each other.
- at least two of R 2 s may be the same of differ from each other.
- at least two of R 3 s may be the same or differ from each other.
- b1 to b3 may each independently be 0, 1, or 2.
- R 1 to R 3 may be -Br or -OH when b1 to b3 are each 1; and R 1 to R 3 may be -Cl when b1 to b3 are each 2.
- two R 1 s, two R 2 s, and two R 3 s may be in a para position when b1 to b3 are each 2.
- n1 to n3 may each independently be an integer of 0 to 10.
- n1 to n3 may each independently be an integer of 0 to 3.
- embodiments are not limited thereto.
- the composition for destroying microalgae or mosses may include at least one of compounds represented by Formulae 1-1 to 1-6, 2-1 to 2-6, and 3-1 to 3-6 or a salt thereof as an active ingredient.
- embodiments are not limited thereto:
- a 1 to A 3 may have the same definitions as those described above.
- a 1 to A 3 may each independently be selected from groups represented by Formulae 5-1 to 5-23.
- * is a binding site to a neighboring atom; and n1 to n3 may each independently be an integer of 0 to 3.
- the composition for deconstructing microalgae or mosses may include at least one of compounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 or a salt thereof as an active ingredient.
- embodiments are not limited thereto:
- An effect of destroying microalgae or mosses, and in particular, harmful algae causing green tide or red tide, is influenced by the chemical structure of a specific substituent of a compound included in the composition for destroying microalgae or mosses. Accordingly, to increase the effect of destroying microalgae or mosses, a substituent having good algicidal activity is required.
- the composition for destroying microalgae or mosses may need to have good algicidal activity that is strong enough to destroy algae when a small amount of the composition is used, without causing secondary contamination.
- a compound represented by Formula 1 including a benzylamine group, a compound represented by Formula 2 including a benzamide group, and a compound represented by Formula 3 including a phenyl prophenone group have good algicidal activity.
- a C 1 -C 10 alkyl group may refer to a monovalent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms.
- Non-limiting examples of the C 1 -C 10 alkyl group are a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.
- a C 1 -C 10 alkoxy group may refer to a monovalent group represented by -OA 101 (wherein A 101 is a C 1 -C 10 alkyl group as described above.
- a 101 is a C 1 -C 10 alkyl group as described above.
- Non-limiting examples of the C 1 -C 10 alkoxy group are a methoxy group, an ethoxy group, and a propoxy group.
- a C 2 -C 10 alkenyl group may refer to a hydrocarbon group including at least one carbon double bond in the middle or terminal of the C 2 -C 10 alkyl group.
- Non-limiting examples of the C 2 -C 10 alkenyl group are an ethenyl group, a prophenyl group, and a butenyl group.
- a C 2 -C 10 alkynyl group may refer to a hydrocarbon group including at least one carbon triple bond in the middle or terminal of the C 2 -C 10 alkyl group.
- Non-limiting examples of the C 2 -C 10 alkynyl group are an ethynyl group and a propynyl group.
- a C 3 -C 10 cycloalkyl group may refer to a monovalent, monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms.
- Non-limiting examples of the C 3 -C 10 cycloalkyl group are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
- a C 1 -C 10 heterocycloalkyl group may refer to a monovalent monocyclic group having 1 to 10 carbon atoms in which at least one hetero atom selected from N, O, P, and S is included as a ring-forming atom.
- Non-limiting examples of the C 1 -C 10 heterocycloalkyl group are a tetrahydrofuranyl group and a tetrahydrothiophenyl group.
- a C 3 -C 10 cycloalkenyl group may refer to a monovalent monocyclic group having 3 to 10 carbon atoms and including at least one double bond in the ring, but not having aromaticity.
- Non-limiting examples of the C 3 -C 10 cycloalkenyl group are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
- a C 1 -C 10 heterocycloalkenyl group may refer to a monovalent monocyclic group having 1 to 10 carbon atoms, including at least one hetero atom selected from N, O, P, and S as a ring-forming atom, and having at least one double bond in the ring.
- Non-limiting examples of the C 1 -C 10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group.
- a C 6 -C 60 aryl group may refer to a monovalent, aromatic carbocyclic group having 6 to 60 carbon atoms.
- Non-limiting examples of the C 6 -C 60 aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group.
- the C 6 -C 60 aryl group includes at least two rings, the rings may be fused to each other.
- a C 1 -C 60 heteroaryl group may refer to a monovalent, aromatic carbocyclic group having 1 to 60 carbon atoms and including at least one hetero atom selected from N, O, P, and S as a ring-forming atom.
- Non-limiting examples of the C 1 -C 60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
- the C 1 -C 60 heteroaryl includes at least two rings, the rings may be fused to each other.
- At least one substituent of the substituted C 1 -C 10 alkyl group, the substituted C 2 -C 10 alkenyl group, the substituted C 2 -C 10 alkynyl group, the substituted C 1 -C 10 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, and the substituted C 1 -C 60 heteroaryl group may be selected from deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, and a C 1 -C 10 alkyl group.
- a salt of a compound according to the one or more embodiments may be prepared in the same reaction system during final separation, purification, and synthesis processes, or may be prepared separately by reaction with an inorganic base or an organic base.
- a compound according to one or more embodiments includes an acidic group, the compound may form a salt with a base.
- this salt may include, but is not limited to, an alkali metal salt such as a lithium salt, a sodium salt or a potassium salt; an alkali earth metal salt such as a barium salt or calcium salt; other metal salts such as a magnesium salt; an organic base salt such as a salt of dicyclohexylamine; and a salt of a basic amino acid such as lysine or arginine.
- an alkali metal salt such as a lithium salt, a sodium salt or a potassium salt
- an alkali earth metal salt such as a barium salt or calcium salt
- other metal salts such as a magnesium salt
- an organic base salt such as a salt of dicyclohexylamine
- a salt of a basic amino acid such as lysine or arginine.
- this acid addition salt may include, but are not limited to, an inorganic acid, and in particular, a salt of a hydrohalogenic acid (e.g., hydrofluoric acid, hydrobromic acid, hydroiodic acid or hydrochloric acid), nitric acid, carbonic acid, sulfuric acid, or phosphoric acid; a salt of a low alkyl sulfonic acid such as methanesulfonic acid, trifluoromethanesulfonic acid, or ethanesulfonic acid; a salt of benzenesulfonic acid or p-toluene sulfonic acid; a salt of an organic carboxylic acid such as acetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, or citric acid; and a salt of an amino acid such as glutamic acid or aspartic acid.
- a hydrohalogenic acid e.g., hydrofluoric acid, hydro
- the compound according to one or more embodiments may include a derivative in the form of a hydrate or a solvate of the compound ( J. M. Keith, 2004, Trahedron Letters, 45(13), 2739-2742 ).
- the compound according to the one or more embodiments may be isolated from nature or may be prepared using a chemical synthesis method known in the art, for example, usually by reacting a substituent compound with an appropriate reaction solvent to obtain an intermediate product and then reacting the intermediate product in a suitable reaction solvent.
- the reaction solvent which may be used in the preparation process is not specifically limited as long as it is not involved in a reaction.
- the reaction solvent may include ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as dichloromethane and chloroform; amines such as pyridine, piperidine, and triethylamine; acetone; alkyl ketones such as methyl ethyl ketone and methyl isobutyl; alcohols such as methanol, ethanol and propanol; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and hexamethylphosphoric triamide.
- a solvent capable of isolating water during reaction with a Dean-Stark trap may be used.
- examples of such a solvent include benzene, toluene, xylene, and the like.
- separation and purification of a reaction product may be carried out through a process that is usually performed such as concentration, extraction, and the like. For example, separation and purification may be performed through a purification process by column chromatography on silica gel if needed.
- the present disclosure may also include any modification of methods of preparing compounds according to the one or more embodiments, wherein an intermediate product obtained in any step may be used as a starting material for the remaining steps, wherein the starting material may be formed in a reaction system under reaction conditions, and the reaction components may be used in the form of a salt or an optical enantiomer.
- any possible isomer forms for example, substantially pure geometric (cis or trans) isomers, optical isomers (enantiomers), or racemates may also be within the scope of the present invention.
- a method of destroying microalgae or mosses by using the composition for destroying microalgae or mosses may include treating a moss cultivation facility, a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur, with the composition for destroying microalgae or mosses, according to the one or more embodiments.
- the microalgae or mosses may be algae or mosses which may cause green tide or red tide or which may have a biodiesel-producing ability.
- the algae may be selected from blue-green algae, diatoms, green algae, euglenoid algae, flagellates, yellow-green algae, Dinophyta, Raphidophytes, and algae with a biodiesel-producing ability.
- embodiments are not limited thereto.
- Mosses refer to plants belonging to Bryophyta or mosses that mostly grow in wet or shady areas.
- the mosses may be selected from the class Takakiopsida, the class Sphagnopsida, the class Andreaeopsida, the class Andreaeobryopsida, the class Oedipodiopsida, the class Polytrichopsida, the class Tetraphidopsida, and the class Bryopsida.
- embodiments are not limited thereto.
- the blue-green algae may be selected from the genus Microcystis, the genus Anabaena, the genus Aphanizomenon, and the genus Oscillatoria. However, embodiments are not limited thereto.
- the diatoms may be selected from the genus Synedra, the genus Asterionella, the genus Cyclotella, the genus Melosira, the genus Skeletonema costatum, the genus Chaetoceros, the genus Thalassiosira, the genus Leptocylindrus, the genus Nitzschia, the genus Cylindrotheca, the genus Eucampia, and the genus Odontella.
- embodiments are not limited thereto.
- the green algae may be selected from the genus Closterium, the genus Pediastrum, and the genus Scenedesmus. However, embodiments are not limited thereto.
- the euglenoid algae may be of the genus Trachelomonas or the genus Euglena. However, embodiments are not limited thereto.
- the flagellates may be selected from algae of the genus Peridinium, the genus Heterosigma, the genus Heterocapsa, the genus Cochlodinium, the genus Prorocentrum, the genus Ceratium, the genus Noctiluca, the genus Scrippsiella, the genus dinophysis, the genus Alexandrium, the genus Eutreptiella, the genus Pfiesteria, the genus Chattonella, the genus Emiliania, and the genus Gymnodinium.
- embodiments are not limited thereto.
- the yellow-green algae may be of the genus Uroglena. However, embodiments are not limited thereto.
- the Dinophyta and the raphidophytes may be selected from the genus Heterosigma, the genus Heterocapsa, the genus Cochlodinium, the genus Prorocentrum, the genus Ceratium, the genus Noctiluca, the genus Scrippsiella, the genus dinophysis, the genus Alexandrium, the genus Eutreptiella, the genus Pfiesteria, the genus Chattonella, the genus Emiliania, and the genus Gymnodinium.
- embodiments are not limited thereto.
- the algae with a biodiesel-producing ability may be selected from the genus Pseudochoricystis, the genus Botryococcus, and the genus Dunaliella. However, embodiments are not limited thereto.
- the use amount of the composition may be appropriately selected such that a final concentration of the composition remaining in the treated area reaches 1 ⁇ M to 100 ⁇ M, for example, about 1 ⁇ M to 30 ⁇ M.
- compositions for destroying microalgae or mosses will now be described in detail with reference to the following examples. However, these examples are only for illustrative purposes and are not intended to limit the scope of the one or more embodiments of the present disclosure.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of N'-(3,4-dichloro-benzyl)-N,N-diethyl-ethane-1,2-diamine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of N'-(3,4-Dichloro-benzyl)-N,N-dimethyl-ethane-1,2-diamine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of 3,4-dichloro-benzyl)-(2-methoxy-ethyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of (3,4-dichloro-benzyl)-(4,4-dimethoxy-butyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (3,4-dichloro-benzyl)-(3-methyl-butyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of N'-(3,4-dichloro-benzyl)-N,N-dimethyl-propane-1,3-diamine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of 3,4-dichloro-N-(2-diethylamino-ethyl)-benzamide.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow solid of 3,4-Dichloro-N-(2-dimethylamino-ethyl)-benzamide.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a red solid of 3,4-dichloro-N-(3-dimethylamino-propyl)-benzamide.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow solid of 3,4-dichloro-N-(3-diethylamino-propyl)-benzamide.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of (3,4-Dichloro-benzyl)-ethyl-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of (3,4-Dichloro-benzyl)-propyl-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-phenyl-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of butyl-(3,4-dichloro-benzyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (4-Chloro-phenyl)-(3,4-dichlorobenzyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (3,4-dichloro-benzyl)-(4-fluoro-phenyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (4-Bromo-phenyl)-(3,4-dichloro-benzyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a red liquid of (3,4-dichloro-benzyl)-pyridin-2-ylmethyl-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-pyridin-3-ylmethyl-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-pyridin-4-ylmethyl-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow liquid of benzyl-(3,4-dichloro-benzyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-(2-pyridin-3-yl-ethyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a dark-yellow liquid of (3,4-Dichloro-benzyl)-(2-pyridin-2-yl-ethyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-red liquid of (2-Bromo-benzyl)-(2-pyridin-2-yl-ethyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow liquid of (3-Bromo-benzyl)-(2-pyridin-2-yl-ethyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a white liquid of (3,4-dichloro-benzyl)-indan-1-yl-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of cyclobutyl-(3,4-dichloro-benzyl)-amine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid N,N-dibutyl-N'-(3,4-dichlorobenzyl)ethane-1,2-diamine.
- the resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of N,N-dibutyl-N'-(3,4-dichlorobenzyl)propane-1,3-diamine.
- microalgae-destroying effects of Compounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 were analyzed by measuring the half-maximal inhibitory concentration (IC 50 ), which represents the concentration of each compound that is required for 50% inhibition of a total microalgae cell count.
- IC 50 half-maximal inhibitory concentration
- Equation 1 Y represents an algicidal activity (%) at an inoculation concentration of each compound, A and D represent a maximum algicidal activity (%) and a minimum algicidal activity (%), respectively, at an inoculation concentration of each compound, C represents an IC 50 value within an inoculation concentration range, and B represents Hillslope (i.e., a slope of the four-parameter logistic curve which will be described below).
- Algicidal activity % 1 ⁇ Tt / Ct ⁇ 100
- T (treatment group) and C (control group) represent algae densities in cell counts when each compound was inoculated and was not inoculated, respectively, and t represents the number of days which had passed after the inoculation.
- the above-listed microalgae were cultured in a culture flask at a temperature of about 20°C under light conditions, and a medium used was Guillard's f/2 medium which is commonly used in the art ( Guillard RRL and Keller MD. Culturing dinoflagellates. In: Spector (Ed.), Dinoflagellates. New York: Academic Press; 1984, 391442 ).
- Microcystis aeruginosa was treated with Compounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 at concentrations of 0.1 uM, 0.2 uM, 0.5 uM, 1 uM, 2 uM, 5 uM, 10 uM, 15 uM, and 20 uM and then cultured for 5 days.
- Control groups were not treated with any of the compounds synthesized in the above-identified examples. After incubation, the number of cells of each alga was counted using a Burker-Tukr hemocytometer, and IC 50 values were calculated according to Equation 1 using SigmaPlot Version 11.2 software (Standard curve: the four-parameter logistic curve). The results are shown in Tables 1 and 2.
- Example 1 Compound Chattonella Marina Heterocapsa Circularisquama Cochlodinium Polykrikoides Heterosigma Akashiwo Microcystis aeruginosa 3,4-dichlorobenzylamines Example 1 1 2.9 1.76 2.3 1.58 4.89 Example 2 2 2.6 3.4 0.327 1.3 0.57
- Example 3 3 >5 3.1 >5 2.25 8.41
- Example 5 5 >5 >5 >5 >5 1.3 14.17
- Example 6 6 >5 4.8 4.417 1.3 8.64
- Example 7 7 2 1.5 1.53 0.28 11.61
- Example 8 0.81 3.3 0.29 1.26 0.09
- Example 17 >5 >5 >5 >5 1.18 >20
- Example 18 18 2.67 >5 4.38 0.73 11.83
- Example 19 19 3.5 >5 4.14 1.27 13.8
- Example 20 3.16 2.86 3.516 0.44 >20
- Example 21 21 >5 3.3 3.6 1.28 9.66
- Example 23 23 >5 >5 >5 1.5
- IC 50 value greater than 5 means nearly zero microalgae-filling effect.
- Example 35 To investigate a microalgae-destroying effect of Compound 35 synthesized in Example 35, culture solutions of Chattonella Marina, Heterosigma Circularisquama, Cochlodinium Polykrikoides, and Heterosigma akashiwo (40 mL, initial population number: about 15X10 4 to 18X10 4 /mL) were each treated with a solution of Compound 35 (1 ⁇ M in dimethyl sulfoxide (DMSO) and f/2 medium) for about 6 hours. A microalgae culture solution not treated with a solution of Compound 35 was used as a control group. After the treatment, viable cell ratios of the microalgae with respect to time were measured, and it was also observed whether the microalgae were destroyed. The results are shown in FIGS. 1 and 2 .
- DMSO dimethyl sulfoxide
- the viable cell ratios of the microalgae were found to have decreased with time, indicating that Compound 35 had a high algicidal effect on the four kinds of the microalgae.
- FIG. 2 shows microscope images of the four microalgal species observed after the treatment with Compound 35, wherein (a), (b), (c), and (d) represent microscope images of Cochlodinium Polykrikoides, Heterosigma akashiwo, Heterosigma circularisquama, and Chattonella Marina, respectively, and (a)-1, (a)-3, (b)-1, (c)-1, and (d)-1 represent control groups not treated with Compound 35.
- FIG. 2 the four microalgal species treated with Compound 35 were found to have been destroyed, as shown in (a)-2, (a)-4, (b)-2, (b)-3, (c)-2, (c)-3, (d)-2, and (d)-3 of FIG. 2 .
- Compound 2 was found to have a high algicidal effect on the Microcystis.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Chemical & Material Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cultivation Of Seaweed (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
- The present disclosure relates to a composition for destruction of microalgae or mosses.
- Microalgae as photosynthetic aquatic unicellular organisms are commonly referred to as phytoplankton. Currently, active efforts are ongoing worldwide to utilize microalgae industrially. Microalgae may be used for wastewater treatment, immobilization of carbon dioxide, and the like, due to their diverse abilities, and have been used for production of useful materials such as fuel materials, cosmetics, feed, food coloring materials, and medicinal raw materials, while their fields of application have been widened due to the continuous discovery of useful value-added materials from microalgae.
- Microalgae, as a biological resource which is free of the criticism on the use of food resources for energy production, may generate biofuels having similar physical properties to petroleum diesel. An energy conversion process for producing biodiesel from microalgae involves production and harvest of microalgae biomass, a process of oil extraction from the microalgae biomass, and a transesterification reaction of the extracted oil. In particular, the process of oil extraction from microalgae, which is controversial due to its high cost, is regarded as a bottleneck in high lipid productivity and biodiesel production. Accordingly, an efficient oil extraction apparatus and method are required prior to the production of biodiesel from microalgae.
- On the other hand, microalgae also include harmful algae which result in abnormal proliferation of algae such as that of a green tide or red tide phenomenon. Green tide refers to a phenomenon in which the color of water turns into a prominent green color due to overproliferation and aggregation of floating algae, i.e., phytoplankton, on the water surface of a eutrophic lake or a river with a slow stream. In general, this green tide occurs only in freshwater, and may be caused by the inflow of various land pollutants such as industrial wastewater, domestic sewage, fertilizers, pesticides, and livestock and human manure, into a river or lake, wherein these pollutants are deposited in the lower portion of the body of water and decomposed by bacteria into organic matter, which then generates nitrogen and phosphorus which is fed on by plankton, thus causing green tide in seawater and fresh water. Such green tide may reduce dissolved oxygen in water, and generate toxic algae and various green plankton, killing fish and aquatic organisms. Furthermore, heavy metals deposited at the bottom of the waters may flow in the waters to thereby contaminate fresh water and poison fish, further causing other problems such as environmental destruction and damage to natural aesthetics. Organisms that cause green tide are green algae, diatoms, blue-green algae, and phytomastigophora. Of these organisms, blue-green algae are the main cause of green tide. On the other hand, red tide refers to a phenomenon in which the color of seawater turns red, reddish brown, tan, green, yellow-green, or yellow due to abnormal proliferation of plankton caused by massive inflows of organic contaminants, nitrogen, phosphorus, and the like from land. Organisms which cause such red tide are mainly flagellates and diatoms.
- Such green tide and red tide caused by harmful algae may rapidly lead to an oxygen-deficient condition in the sea, due to the depletion of dissolved oxygen in the water, which consequently results in the mass death of fish and shellfish. Overproliferated plankton may adhere to the gills of fish such as to choke the fish. Flagellates such as Cochlodinium may generate harmful toxins which kill fish. Currently, about 50% of animal proteins consumed by about two billion of the world's population are supplied from the sea. Accordingly, the destruction of marine ecosystems by red tide may have a serious impact on such food resources, deteriorating the utility value of waters, and further raising more serious environmental issues beyond economic values.
- As described above, microalgae may not only generate bioenergy but may also mitigate harmful environmental problems. To utilize such microalgae, there is required an oil extraction process for destruction of the cell membranes of microalgae to increase yield of extracted intracellular lipids. Typical oil extraction methods used so far are a solvent extraction method (Chiara Samori et al., Bioresource Technology, 101:3274, 2010), a Soxhlet extraction method (Ayhan Demirbas a and M. Fatih Demirbas, Energy Conversion and Management, 52(2011):163, 2011), a supercritical extraction method (Mohamed El Hattab et al., Journal of Chromatography A, 1143:1, 2007), an osmotic impact method (Jae-Yon Lee et al., Bioresource Technology, 101:575, 2010), an electromagnetic wave and sonic extraction method (Choi I et al., Journal of Fooe Processing and Preservation, 30(4):40, 2010), a cracking or hydrocracking method (Zecchina A et al., Chem A Eur J, 13:2440, 2007), and a pyrolysis method (Miao X and Wu Q, J Biotechnol, 110:85, 2004).
- However, these methods have drawbacks such as low extraction yield, high operation costs, complexity, and the like. Accordingly, for efficient oil extraction from microalgae, it is necessary to develop a simpler, more efficient pretreatment method.
- For mosses, various nitrogen compounds may be generated from dead mosses, and mass proliferation of mosses may also cause green tide. Mosses may adhere to glass or walls, causing aesthetic unpleasantness in an aquarium, an exhibition hall, and the like, while deteriorating the water quality and functionality of a household water tank or industrial facilities such as a large water tank, a water storage tank, or an aquafarm. Therefore, it is also necessary to manage mosses in order to prevent and eliminate mosses.
- Accordingly, the inventors of the present disclosure found that a benzylamine compound, a benzamide compound, and/or a phenyl propenone compound, each having a specific substituent, may have an effect of destroying the cell membranes of microalgae, thus completing the present invention.
- The present disclose provides a composition for destroying microalgae or mosses, and a method of destroying microalgae or mosses by using the composition, wherein the composition includes a benzyl amine compound, a benzamide compound, and/or a phenyl propenone compound, each having a microalgae or mosses destruction effect.
-
- wherein, in Formulae 1 to 3,
- A1 to A3 may each independently be selected from hydrogen, deuterium, - N(R11)(R12), a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group,
- R1 to R3, R11, and R12 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, and a substituted or unsubstituted C1-C10 alkoxy group,
- b1 to b3 may each independently be selected from an integer of 0 to 5, wherein at least two R1s are the same as or different from each other when b1 is 2 or greater, at least two R2s are the same as or different from each other when b2 is 2 or greater, and at least two R3s are the same as or different from each other when b3 is 2 or greater,
- n1 to n3 may each independently be selected from an integer of 0 to 10, and
- at least one substituent of the substituted C1-C10 alkyl group, the substituted C2-C10 alkenyl group, the substituted C2-C10 alkynyl group, the substituted C1-C10 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, and the substituted C1-C60 heteroaryl group is selected from deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, and a C1-C10 alkyl group.
- According to another aspect of the present disclosure, there is provided a method of destroying microalgae or mosses, the method including treating a moss cultivation facility, a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur, with the above-described composition for destroying microalgae or mosses.
- As used herein, the term "area" may refer to a region under the environment where green tide or red tide likely occurs, including any aquatic environments including both seawater and fresh water. The term "treating" or "treatment" may refer to contacting microalgae or mosses with the composition according to one or more embodiments, and may include adding the composition according to one or more embodiments to water including the microalgae or mosses such as to make the composition contact the composition. The adding of the composition may include spraying the composition onto the water surface, or a stirring step, which may optionally be performed while moving over the water surface.
- In some embodiments, the method may use an out-of-water treatment method. The term "out-of-water treatment method" may refer to drawing water from a water system, treating the water with the composition for destroying microalgae or mosses to remove the microalgae or mosses, and then discharging treated water back into the water system. The term "water system" may refer to a water supply source, for example, natural water systems such as water reservoirs, lakes, rivers, and the like, and artificial water systems such as aquafarms, fishing spots, cultivation facilities, water zone in golf courses, water storage tanks, and the like. For example, the method may include: drawing raw water including microalgae or mosses from a water system; treating the raw water with the composition according to one or more embodiments; and discharging treated water back into the water system. To prevent red tide or green tide which may occur due to nutritive salts if they are released together with the treated water, the method according to one or more embodiments may further include removing the remaining composition, the remaining microalgae or mosses, organic material, nutritive salts, and dead microalgae or mosses. The removing step may include a physical method such as precipitation, solid-liquid separation, or simple filtration, or a chemical method using copper sulfate, a chlorine-based material, ultraviolet rays, ozone, or the like.
- The method according to one or more embodiments may further include, before the treatment with the composition according to one or more embodiments, treating raw water with a flocculant to flocculate the algae . The resulting aggregate produced by the flocculant may be removed by floating it using air bubbles or by precipitation, and then the water (supernatant) from which the aggregate has been removed may be treated with the composition according to one or more embodiments, which may have advantages in terms of cost, since a lower amount of the composition may be used, and prevention of side effects which may likely occur from release of a high concentration of the composition. Examples of the flocculant may be aluminum sulfate, ferric sulfate, ferric chloride, polyaluminum chloride, polyaluminum silicate sulfate, polyhydroxy aluminum silicate chloride, or polyamines. An auxiliary flocculant, for example, sodium alginate, sodium silicate, bentonite, or kaolin, may be used. For example, an acidic or alkaline pH adjuster may be used.
- In some other embodiments, the method according to one or more embodiments may use an in-water treatment method. The term "in-water treatment method" may refer to removing microalgae or mosses by spraying the composition according to one or more embodiments into a water system. Since the composition according to one or more embodiments is less toxic to other living organisms than to algae, the composition may be sprayed in an appropriate concentration range such as to treat the microalgae or mosses. The concentration of the composition may be appropriately adjusted according to a type of a water system to be treated, a pH, a salt concentration, a temperature, a composition, an area, a depth, a use, or aquatic organic distribution of the water system, types of microalgae or mosses to be treated, a concentration or distribution of the microalgae or mosses, a purpose of destruction of microalgae or mosses, a targeted achievement from the destruction, or the like. Like the "out-of-water treatment method," the "in-water treatment method" may further include removing the remaining composition, the remaining microalgae or mosses, organic material, nutritive salts, and dead microalgae or mosses. The removing step may include physical filtration using a filter such as filter paper, or may include floating the remaining materials as described above by spraying a flocculant at the same time as or sequently so as to remove the remaining materials. The removing step may include generating air bubbles to supply oxygen to water, increase efficiency, and allow the flocculation to float without settling.
- According to another aspect of the present disclosure, the composition according to one or more embodiments may be used to prevent green tide or red tide caused from microalgae or mosses. In this case, due to the presence of a small amount of microalgae or mosses, and a microalgae or mosses generation preventing effect of the composition according to one or more embodiments remaining after use, the amount of the composition may be further reduced. However, dead microalgae or mosses may function as nutritive salts contributing to the occurrence of green tide or red tide. Accordingly, together with) the in-water or out-of-water treatment method, a physical filtration, chemical treatment, or air bubble generation step may be further included.
- As described above, when a moss cultivation facility, a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur is treated with the composition for destroying microalgae or mosses, according to the one or more embodiments, growth and proliferation of microalgae may be inhibited, and damage from red tide and/or green tide may be prevented.
-
-
FIG. 1 shows viable cell ratios of four types of microalgae of Chattonella Marina, Heterosigma circularisquama, Cochlodinium Polykrikoides, and Heterosigma with respect to time, when culture solutions of the four microalgae were each treated withCompound 35 of Example 1 in Evaluation Example 2. -
FIG. 2 shows microscope images as results of the treatment of the four microalgae withCompound 35 in Evaluation Example 2, wherein (a), (b), (c) and (d) represent Cochlodinium Polykrikoides, Heterosigma, Heterosigma circularisquama, and Chattonella Marina, respectively; and (a)-1, (a)-3, (b)-1, (c)-1, and (d)-1 represent control groups of the microalgae not treated withCompound 35. -
FIG. 3 shows viable cell counts of Microcystis with respect to time when Microcystis was treated withCompound 2 inEvaluation 2. -
FIG. 4 shows a result of a toxicity test performed on Daphnia magna according to Evaluation Example 3 usingCompounds -
FIG. 5 shows a result of a toxicity test performed on Danio rerio according to Evaluation Example 4 usingCompounds -
- In
Formulae 1 to 3, A1 to A3 may each independently be selected from hydrogen, deuterium, -N(R11)(R12), a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group, and - R11 and R12 may each independently be selected from hydrogen, deuterium, -F, - Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, and a substituted or unsubstituted C1-C10 alkoxy group.
- For example, in
Formulae 1 to 3, A1 to A3 may each independently be selected from -N(R11)(R12), a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C10 aryl group, and a substituted or unsubstituted C1-C10 heteroaryl group. However, embodiments are not limited thereto. -
- In Formulae 4-1 to 4-16, * is a binding site to a neighboring atom.
- In Formulae 4-1 to 4-16, R11 to R14, and R21 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, and a substituted or unsubstituted C1-C10 alkyl group.
- For example, in Formulae 4-1 to 4-16, R11 to R14 may each independently be selected from
a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group; and
a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each substituted with -OH group, and
R21 may be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and -OH. However, embodiments are not limited thereto.
In Formulae 4-1 to 4-16,
b11 may be an integer of 0 to 2,
b12 may be an integer of 0 to 3,
b13 may be an integer of 0 to 4,
b14 may be an integer of 0 to 5,
b15 may be an integer of 0 to 6, and
b16 may be an integer of 0 to 7,
wherein b11 indicates the number of R21s. For example, when b11 is 2 or greater, at least two of R21s may be the same or differ from each other. The meanings of b12 to b16 may also be understood based on the description of b11 and the structures of Formula 4-1 to 4-16. - For example, in Formulae 4-1 to 4-16, b11 to b16 may each independently be 0 or 1.
-
- In Formulae 5-1 to 5-23, * is a binding site to a neighboring atom.
- In
Formulae 1 to 3, R1 to R3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, and a substituted or unsubstituted C1-C10 alkoxy group. - For example, in
Formulae 1 to 3, R1 to R3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, and a substituted or unsubstituted C1-C10 alkyl group. However, embodiments are not limited thereto. - For example, in
Formulae 1 to 3, R1 to R3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and -OH. - In
Formulae 1 to 3, b1 to b3 may each independently be an integer of 0 to 5. When b1 is 2 or greater, at least two of R1s may be the same or differ from each other. When b2 is 2 or greater, at least two of R2s may be the same of differ from each other. When b3 is 2 or greater, at least two of R3s may be the same or differ from each other. - For example, in
Formulae 1 to 3, b1 to b3 may each independently be 0, 1, or 2. - In some embodiments, in
Formulae 1 to 3, R1 to R3 may be -Br or -OH when b1 to b3 are each 1; and R1 to R3 may be -Cl when b1 to b3 are each 2. - In some embodiments, in
Formulae 1 to 3, two R1s, two R2s, and two R3s may be in a para position when b1 to b3 are each 2. - In
Formulae 1 to 3, n1 to n3 may each independently be an integer of 0 to 10. - For example, in
Formulae 1 to 3, n1 to n3 may each independently be an integer of 0 to 3. However, embodiments are not limited thereto. -
- In Formulae 1-1 to 1-6, Formulae 2-1 to 2-6, and Formulae 3-1 to 3-6, A1 to A3, and n1 to n3 may have the same definitions as those described above.
-
- In Formulae 5-1 to 5-23, * is a binding site to a neighboring atom; and n1 to n3 may each independently be an integer of 0 to 3.
-
- An effect of destroying microalgae or mosses, and in particular, harmful algae causing green tide or red tide, is influenced by the chemical structure of a specific substituent of a compound included in the composition for destroying microalgae or mosses. Accordingly, to increase the effect of destroying microalgae or mosses, a substituent having good algicidal activity is required. The composition for destroying microalgae or mosses may need to have good algicidal activity that is strong enough to destroy algae when a small amount of the composition is used, without causing secondary contamination.
- The inventors of the present disclosure found that a compound represented by
Formula 1 including a benzylamine group, a compound represented byFormula 2 including a benzamide group, and a compound represented byFormula 3 including a phenyl prophenone group have good algicidal activity. - As used herein, a C1-C10 alkyl group may refer to a monovalent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms. Non-limiting examples of the C1-C10 alkyl group are a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.
- As used herein, a C1-C10 alkoxy group may refer to a monovalent group represented by -OA101 (wherein A101 is a C1-C10 alkyl group as described above. Non-limiting examples of the C1-C10 alkoxy group are a methoxy group, an ethoxy group, and a propoxy group.
- As used herein, a C2-C10 alkenyl group may refer to a hydrocarbon group including at least one carbon double bond in the middle or terminal of the C2-C10 alkyl group. Non-limiting examples of the C2-C10 alkenyl group are an ethenyl group, a prophenyl group, and a butenyl group.
- As used herein, a C2-C10 alkynyl group may refer to a hydrocarbon group including at least one carbon triple bond in the middle or terminal of the C2-C10 alkyl group. Non-limiting examples of the C2-C10 alkynyl group are an ethynyl group and a propynyl group.
- As used herein, a C3-C10 cycloalkyl group may refer to a monovalent, monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms. Non-limiting examples of the C3-C10 cycloalkyl group are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
- As used herein, a C1-C10 heterocycloalkyl group may refer to a monovalent monocyclic group having 1 to 10 carbon atoms in which at least one hetero atom selected from N, O, P, and S is included as a ring-forming atom. Non-limiting examples of the C1-C10 heterocycloalkyl group are a tetrahydrofuranyl group and a tetrahydrothiophenyl group.
- As used herein, a C3-C10 cycloalkenyl group may refer to a monovalent monocyclic group having 3 to 10 carbon atoms and including at least one double bond in the ring, but not having aromaticity. Non-limiting examples of the C3-C10 cycloalkenyl group are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
- As used herein, a C1-C10 heterocycloalkenyl group may refer to a monovalent monocyclic group having 1 to 10 carbon atoms, including at least one hetero atom selected from N, O, P, and S as a ring-forming atom, and having at least one double bond in the ring. Non-limiting examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group.
- As used herein, a C6-C60 aryl group may refer to a monovalent, aromatic carbocyclic group having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group includes at least two rings, the rings may be fused to each other.
- As used herein, a C1-C60 heteroaryl group may refer to a monovalent, aromatic carbocyclic group having 1 to 60 carbon atoms and including at least one hetero atom selected from N, O, P, and S as a ring-forming atom. Non-limiting examples of the C1-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl includes at least two rings, the rings may be fused to each other.
- At least one substituent of the substituted C1-C10 alkyl group, the substituted C2-C10 alkenyl group, the substituted C2-C10 alkynyl group, the substituted C1-C10 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, and the substituted C1-C60 heteroaryl group may be selected from deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, and a C1-C10 alkyl group.
- As used herein, a salt of a compound according to the one or more embodiments may be prepared in the same reaction system during final separation, purification, and synthesis processes, or may be prepared separately by reaction with an inorganic base or an organic base. When a compound according to one or more embodiments includes an acidic group, the compound may form a salt with a base. For example, this salt may include, but is not limited to, an alkali metal salt such as a lithium salt, a sodium salt or a potassium salt; an alkali earth metal salt such as a barium salt or calcium salt; other metal salts such as a magnesium salt; an organic base salt such as a salt of dicyclohexylamine; and a salt of a basic amino acid such as lysine or arginine. When a compound according to one or more embodiments includes a basic group in molecular, the compound may form an acid addition salt. Examples of this acid addition salt may include, but are not limited to, an inorganic acid, and in particular, a salt of a hydrohalogenic acid (e.g., hydrofluoric acid, hydrobromic acid, hydroiodic acid or hydrochloric acid), nitric acid, carbonic acid, sulfuric acid, or phosphoric acid; a salt of a low alkyl sulfonic acid such as methanesulfonic acid, trifluoromethanesulfonic acid, or ethanesulfonic acid; a salt of benzenesulfonic acid or p-toluene sulfonic acid; a salt of an organic carboxylic acid such as acetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, or citric acid; and a salt of an amino acid such as glutamic acid or aspartic acid.
- The compound according to one or more embodiments may include a derivative in the form of a hydrate or a solvate of the compound (J. M. Keith, 2004, Trahedron Letters, 45(13), 2739-2742).
- The compound according to the one or more embodiments may be isolated from nature or may be prepared using a chemical synthesis method known in the art, for example, usually by reacting a substituent compound with an appropriate reaction solvent to obtain an intermediate product and then reacting the intermediate product in a suitable reaction solvent.
- The reaction solvent which may be used in the preparation process is not specifically limited as long as it is not involved in a reaction. Examples of the reaction solvent may include ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as dichloromethane and chloroform; amines such as pyridine, piperidine, and triethylamine; acetone; alkyl ketones such as methyl ethyl ketone and methyl isobutyl; alcohols such as methanol, ethanol and propanol; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and hexamethylphosphoric triamide. In particular, among nonreactive organic solvents generally used in organic synthesis, a solvent capable of isolating water during reaction with a Dean-Stark trap may be used. Examples of such a solvent include benzene, toluene, xylene, and the like. However, embodiments are not limited thereto. Separation and purification of a reaction product may be carried out through a process that is usually performed such as concentration, extraction, and the like. For example, separation and purification may be performed through a purification process by column chromatography on silica gel if needed.
- The present disclosure may also include any modification of methods of preparing compounds according to the one or more embodiments, wherein an intermediate product obtained in any step may be used as a starting material for the remaining steps, wherein the starting material may be formed in a reaction system under reaction conditions, and the reaction components may be used in the form of a salt or an optical enantiomer.
- According to types of substituents, intermediate products, and a preparation method selected to prepare the compound according to one or more embodiments, any possible isomer forms, for example, substantially pure geometric (cis or trans) isomers, optical isomers (enantiomers), or racemates may also be within the scope of the present invention.
- In accordance with another aspect of the present disclosure, there is provided a method of destroying microalgae or mosses by using the composition for destroying microalgae or mosses, according to the one or more embodiments. The method of destroying microalgae or mosses may include treating a moss cultivation facility, a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur, with the composition for destroying microalgae or mosses, according to the one or more embodiments.
- The microalgae or mosses may be algae or mosses which may cause green tide or red tide or which may have a biodiesel-producing ability. For example, the algae may be selected from blue-green algae, diatoms, green algae, euglenoid algae, flagellates, yellow-green algae, Dinophyta, Raphidophytes, and algae with a biodiesel-producing ability. However, embodiments are not limited thereto.
- Mosses refer to plants belonging to Bryophyta or mosses that mostly grow in wet or shady areas. As used herein, the mosses may be selected from the class Takakiopsida, the class Sphagnopsida, the class Andreaeopsida, the class Andreaeobryopsida, the class Oedipodiopsida, the class Polytrichopsida, the class Tetraphidopsida, and the class Bryopsida. However, embodiments are not limited thereto.
- The blue-green algae may be selected from the genus Microcystis, the genus Anabaena, the genus Aphanizomenon, and the genus Oscillatoria. However, embodiments are not limited thereto.
- The diatoms may be selected from the genus Synedra, the genus Asterionella, the genus Cyclotella, the genus Melosira, the genus Skeletonema costatum, the genus Chaetoceros, the genus Thalassiosira, the genus Leptocylindrus, the genus Nitzschia, the genus Cylindrotheca, the genus Eucampia, and the genus Odontella. However, embodiments are not limited thereto.
- The green algae may be selected from the genus Closterium, the genus Pediastrum, and the genus Scenedesmus. However, embodiments are not limited thereto.
- The euglenoid algae may be of the genus Trachelomonas or the genus Euglena. However, embodiments are not limited thereto.
- The flagellates may be selected from algae of the genus Peridinium, the genus Heterosigma, the genus Heterocapsa, the genus Cochlodinium, the genus Prorocentrum, the genus Ceratium, the genus Noctiluca, the genus Scrippsiella, the genus dinophysis, the genus Alexandrium, the genus Eutreptiella, the genus Pfiesteria, the genus Chattonella, the genus Emiliania, and the genus Gymnodinium. However, embodiments are not limited thereto.
- The yellow-green algae may be of the genus Uroglena. However, embodiments are not limited thereto.
- The Dinophyta and the raphidophytes may be selected from the genus Heterosigma, the genus Heterocapsa, the genus Cochlodinium, the genus Prorocentrum, the genus Ceratium, the genus Noctiluca, the genus Scrippsiella, the genus dinophysis, the genus Alexandrium, the genus Eutreptiella, the genus Pfiesteria, the genus Chattonella, the genus Emiliania, and the genus Gymnodinium. However, embodiments are not limited thereto.
- The algae with a biodiesel-producing ability may be selected from the genus Pseudochoricystis, the genus Botryococcus, and the genus Dunaliella. However, embodiments are not limited thereto.
- When the composition for destroying microalgae or mosses, according to the one or more embodiments, including the compounds represented by
Formulae 1 to 51 or a salt thereof, is used to treat a moss cultivation facility, a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur, the use amount of the composition may be appropriately selected such that a final concentration of the composition remaining in the treated area reaches 1µM to 100µM, for example, about 1µM to 30µM. - One or more embodiments of the composition for destroying microalgae or mosses will now be described in detail with reference to the following examples. However, these examples are only for illustrative purposes and are not intended to limit the scope of the one or more embodiments of the present disclosure.
- All compounds used for synthesis were purchased from Sigma-Aldrich, TCI, Junsei, and Merck. Moisture-sensitive compounds were reacted under a N2 atmosphere.
- Each compound was analyzed by 1H Nuclear magnetic resonance (NMR, YH300, Oxford Instruments) using tetramethylsilane (TMA) in CDCl3 or DMSO as a standard sample at 300MHz and 296K. The chemical shifts in NMR were expressed in parts per million (ppm), and J-coupling constants were expressed in Hertz (Hz).
- After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.664 g (5.714 mmol) of N,N-diethylethylenediamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by thin layer chromatography (TLC). When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of N'-(3,4-dichloro-benzyl)-N,N-diethyl-ethane-1,2-diamine.
Yield: 89.5 %
1H NMR (300 MHz, CDCl3) δ 7.44 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.0 Hz, 1H), δ 7.18 (dd, J=8.0 and 1.8 Hz, 1H), δ 3.76 (s, 1H), δ 2.68 (m, 8H), δ 1.06 (t, J=6.9 Hz, 6H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.744 g (5.714 mmol) of N,N-diethyl-1,3-diaminopropane was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of N'-(3,4-dichloro-benzyl)-N,N-diethyl-propane-1,3-diamine.
Yield: 90. 75%
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.0 Hz, 1H), δ 7.17 (dd, J=8.0 and 1.8 Hz, 1H), δ 3.73 (s, 2H), δ 2.66 (t, J=6.5 Hz, 2H), δ 2.57 (m, 6H), δ 1.72 (m, J=6.5 Hz, 1H), δ 1.05 (t, J=7.3 Hz, 6H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.503 g (5.714 mmol) of N,N-dimethylethylenediamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of N'-(3,4-Dichloro-benzyl)-N,N-dimethyl-ethane-1,2-diamine.
Yield : 93.2 %
1H NMR (300 MHz, CDCl3) δ 7.44 (d, J=2.2 Hz, 1H), δ 7.39 (d, J=8.4 Hz, 1H), δ 7.18 (dd, J=8.4 and 2.2 Hz, 1H), δ 3.76 (s, 2H), δ 2.68 (m, J=5.8 Hz, 2H), δ 2.45 (t, J=5.8 Hz, 2H), δ 2.21 (s, 6H), δ 2.12 (s, 1H) - Example 5
- After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.429 g (5.714 mmol) of 2-methoxyethylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of 3,4-dichloro-benzyl)-(2-methoxy-ethyl)-amine.
Yield : 92.1 %
1H NMR (300 MHz, CDCl3) δ 7.45 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.0 Hz, 1H), δ 7.18 (dd, J=8.0 and 1.8 Hz, 1H), δ 3.76 (s, 2H), δ 3.52 (t, J=5.1 Hz, 2H), δ 3.35 (s, 3H), δ 2.79 (t, J=5.3 Hz, 2H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.761 g (5.714 mmol) of 4-aminobutyraldehyde dimethyl acetal was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of (3,4-dichloro-benzyl)-(4,4-dimethoxy-butyl)-amine.
Yield : 87.15%
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.0 Hz, 1H), δ 7.17 (dd, J=8.0 and 1.8 Hz, 1H), δ 4.38 (t, J=5.49 Hz, 1H), δ 3.74 (s, 2H), δ 3.31 (s, 6H), δ 2.64 (t, 2H), δ 1.69 (m, 4H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.498 g (5.714 mmol) of isoamylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (3,4-dichloro-benzyl)-(3-methyl-butyl)-amine.
Yield: 94 %
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=2.19 Hz, 1H), δ 7.38 (d, J=8.0 Hz, 1H), δ 7.17 (dd, J=8.0 and 2.19 Hz, 1H), δ 3.74 (s, 2H), δ 2.63 (t, 2H), δ 1.70 (m, J=6.9 Hz, 1H), δ 1.42 (m, J=6.9 Hz, 2H), δ 1.28 (b, 1H), δ 0.90 (d, 6H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.583 g (5.714 mmol) of N,N-dimethyl-1,3-propanediamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of N'-(3,4-dichloro-benzyl)-N,N-dimethyl-propane-1,3-diamine.
Yield : 89.9 %
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.4 Hz, 1H), δ 7.17 (dd, J=8.4 and 1.8 Hz, 1H), δ 3.74 (s, 2H), δ 2.66 (t, J=6.9 Hz, 2H), δ 2.34 (t, J=6.9 Hz, 2H), δ 2.22 (s, 6H), δ 1.72 (m, J=6.9 Hz, 3H) - After 1 g (4.774 mmol) of 3,4-dichlorobenzoyl chloride was dissolved in 20 mL of tetrahydrofuran (THF), 0.621 g (4.774 mmol) of N,N-diethylethylenediamine was added thereto, and 1 mL (7.161 mmol) of triethylamine was slowly added and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted three times with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of 3,4-dichloro-N-(2-diethylamino-ethyl)-benzamide.
Yield: 94.1 %
1H NMR (300 MHz, CDCl3) δ 7.90 (d, J=2.1 Hz, 1H), δ 7.62 (dd, J=8.0 and 2.1 Hz, 1H), δ 7.51 (d, J=8.0 Hz, 1H), δ 7.1 (b, 1H), δ 3.51 (m, J=5.1 Hz, 2H), δ 2.69 (t, J=5.1 Hz, 2H), δ 2.63 (m, J=6.9 Hz, 4H), δ 1.08 (t, J=6.9 Hz, 6H) - After 1 g (4.774 mmol) of 3,4-dichlorobenzoyl chloride was dissolved in 20 mL of THF, 0.420 g (4.774 mmol) of N,N-diethylethylenediamine was added thereto, and 1 mL (7.161 mmol) of triethylamine was slowly added and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted three
times 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow solid of 3,4-Dichloro-N-(2-dimethylamino-ethyl)-benzamide.
Yield :95 %
1H NMR (300 MHz, CDCl3) δ 7.91 (d, J=2.2 Hz, 1H), δ 7.65 (dd, J=8.0 and 2.2 Hz, 1H), δ 7.52 (d, J=8.0 Hz, 1H), δ 6.96 (b, 1H), δ 3.55 (m, J=5.8 Hz, 2H), δ 2.58 (t, J=5.8 Hz, 2H), δ 2.30 (s, 6H) - After 1 g (4.774 mmol) of 3,4-dichlorobenzoyl chloride was dissolved in 20 mL of THF, 0.487 g (4.774 mmol) of dimethyl-1,3-propanediamine was added thereto, and 1 mL (7.161 mmol) of triethylamine was slowly added and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted three times with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a red solid of 3,4-dichloro-N-(3-dimethylamino-propyl)-benzamide.
Yield : 97.6 %
1H NMR (300 MHz, CDCl3) δ 9.02 (b, 1H), δ 7.88 (d, J=1.8 Hz, 1H), δ 7.65 (dd, J=8.4 and 1.8 Hz, 1H), δ 7.51 (d, J=8.4 Hz, 1H), δ 3.59 (m, J=5.8 Hz, 2H), δ 2.61 (t, J=5.8 Hz, 2H), δ 2.37 (s, 6H), δ 1.84 (m, J=5.8 Hz, 2H) - After 1 g (4.774 mmol) of 3,4-dichlorobenzoyl chloride was dissolved in 20 mL of THF, 0.621 g (4.774 mmol) of N,N-diethyl-1,3-diaminopropane was added thereto, and 1 mL (7.161 mmol) of triethylamine was slowly added and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted three times with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow solid of 3,4-dichloro-N-(3-diethylamino-propyl)-benzamide.
Yield: 91.2 %
1H NMR (300 MHz, CDCl3) δ 9.31 (b, 1H), δ 7.89 (d, J=2.1 Hz, 1H), δ 7.68 (dd, J=8.4 and 2.1 Hz, 1H), δ 7.51 (d, J=8.4 Hz, 1H), δ 3.59 (m, J=5.4 Hz, 2H), δ 2.68 (m, 6H), δ 1.81 (m, J=5.4 Hz, 2H), δ 1.09 (t, J=6.9 Hz, 6H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.257 g (5.714 mmol) of ethylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of (3,4-Dichloro-benzyl)-ethyl-amine.
Yield : 95.4 %
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=2.1 Hz, 1H), δ 7.38 (d, J=8.4 Hz, 1H), δ 7.17 (dd, J=8.4 and 2.1 Hz, 1H), δ 3.74 (s, 2H), δ 2.69 (m, J=6.9, 2H), δ 1.28 (b, 1H), δ 1.15 (t, J=6.9 Hz, 3H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.337 g (5.714 mmol) of propylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of (3,4-Dichloro-benzyl)-propyl-amine.
Yield : 94.3 %
1H NMR (300 MHz, CDCl3) δ 7.45 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.4 Hz, 1H), δ 7.17 (dd, J=8.4 and 1.8 Hz, 1H), δ 3.73 (s, 2H), δ 2.58 (t, J=7.3 Hz, 2H), δ 1.58 (m, J=7.3 Hz, 2H), δ 1.42 (b, 1H), δ 0.94 (t, J=7.3 Hz, 3H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.532 g (5.714 mmol) of aniline was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-phenyl-amine.
Yield : 87 %
1H NMR (300 MHz, CDCl3) δ 7.45 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.0 Hz, 1H), δ 7.2 (m, 3H), δ 6.76 (tt, J=7.3 and 1.0 Hz, 1H), δ 6.59 (dt, J=7.3 and 1.0 Hz, 2H), δ 4.29 (s, 2H), δ 4.10 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.417 g (5.714 mmol) of buthylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of butyl-(3,4-dichloro-benzyl)-amine.
Yield : 93.4 %
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=2.1 Hz, 1H), δ 7.39 (d, J=8.0 Hz, 1H), δ 7.17 (dd, J=8.0 and 2.1 Hz, 1H), δ 3.74 (s, 2H), δ 2.62 (t, J=6.9 and 7.3 Hz, 2H), δ 1.53 (m, J= 6.9 Hz, 4H), δ 1.25 (b, 1H), δ 0.93 (t, J=7.32 Hz, 3H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.728 g (5.714 mmol) of 4-chloroaniline was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (4-Chloro-phenyl)-(3,4-dichlorobenzyl)-amine.
Yield : 89 %
1H NMR (300 MHz, CDCl3) δ 7.44 (d, J=1.8 Hz, 1H), δ 7.41 (d, J=8.0 Hz, 1H), δ 7.19 (dd, J= 8.0 and 1.8 Hz, 1H), δ 7.13 (dt, J=9.8 and 2.2 Hz, 2H), δ 6.52 (dt, J=9.8 and 2.2 Hz, 2H), δ 4.28 (s, 2H), δ 4.14 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 20 mL of ethanol, 0.686 g (5.714 mmol) of acetophenone was added thereto and completely dissolved. While the resulting mixture was stirred at about 0°C or lower, 1.2 mL of 4M NaOH was slowly dropwise added thereto and stirred at room temperature for about 3 hours. The degree of progress of reaction was confirmed by TLC. When the starting materials were not detected any longer, the resulting reaction product was washed with cold ethanol and then filtered. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a white solid of 3-(3,4-Dichloro-phenyl)-1-phenyl-propenone.
Yield : 73.2 %
1H NMR (300 MHz, CDCl3) δ 8.04 (dt, 2H), δ 7.74 (d, J=1.83 Hz, 1H), δ 7.68 (s, 1H), δ 7.64 (tt, 1H), δ 7.55 (m, 5H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.640 g (5.714 mmol) of 4-fluoroaniline was added thereto and reacted at room temperature for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (3,4-dichloro-benzyl)-(4-fluoro-phenyl)-amine.
Yield: 86 %
1H NMR (300 MHz, CDCl3) δ 7.46 (d, J=1.8 Hz, 1H), δ 7.41 (d, J= 8.0 Hz, 1H), δ 7.21 (dd, J= 8.0 and 1.8 Hz 1H), δ 6.91 (m, 2H), δ 6.53 (m, 2H), δ 4.26 (s, 2H), δ 4.01 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 20 mL of ethanol, 4- 0.883 g (5.714 mmol) of chloroacetophenone was added thereto and completely dissolved. While the resulting mixture was stirred at about 0°C or lower, 1.2 mL of 4M NaOH was slowly dropwise added thereto and stirred at room temperature for about 3 hours. The degree of progress of reaction was confirmed by TLC. When the starting materials were not detected any longer, the resulting reaction product was washed with cold ethanol and then filtered. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a white solid of 3-(3,4-Dichloro-phenyl)-1-phenyl-propenone.
Yield : 75.8 %
1H NMR (300 MHz, CDCl3) δ 7.99 (dt, 2H), δ 7.74 (d, J=1.83 Hz, 1H), δ 7.68 (s, 1H), δ 7.52 (m, 5H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.982 g (5.714 mmol) of 4-bromoaniline was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (4-Bromo-phenyl)-(3,4-dichloro-benzyl)-amine.
Yield : 30.5%
1H NMR (300 MHz, CDCl3) δ 7.44 (d, J=1.8 Hz, 1H), δ 7.41 (d, J=8.0 Hz, 1H), δ 7.26 (tt, 2H), δ 7.19 (dd, J=8.0 and 1.8 Hz, 1H), δ 6.48 (tt, 2H), δ 4.29 (d, 2H), δ 4.16 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.617 g (5.714 mmol) of 2-picolylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a red liquid of (3,4-dichloro-benzyl)-pyridin-2-ylmethyl-amine.
Yield : 73.3 %
1H NMR (300 MHz, CDCl3) δ 8.57 (d, 1H), δ 7.68 (td, J=7.6 and 1.8 Hz, 1H), δ 7.48 (d, J=1.8 Hz, 1H), δ 7.40 (d, J=8.0 Hz, 1H), δ 7.30 (d, J=8.0 Hz, 1H), δ 7.21 (m, 2H), δ 3.90 (s, 2H), δ 3.79 (s, 2H), δ 2.16 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.617 g (5.714 mmol) of 3-icolylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-pyridin-3-ylmethyl-amine.
Yield : 69.8 %
1H NMR (300 MHz, CDCl3) δ 8.57 (d, J=1.8 Hz, 1H), δ 8.53 (dd, J=4.7 and 1.8 Hz, 1H), δ 7.72 (d, J=7.7 Hz, 1H), δ 7.47 (d, J=1.8 Hz, 1H), δ 7.41 (d, J=8.43 Hz, 1H), δ 7.30 (m, 1H), δ 7.20 (dd, J=8.4 and 1.8 Hz, 1H), δ 3.80 (s, 2H), δ 3.77 (s, 2H), δ 2.04 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.617 g (5.714 mmol) of 4-picolylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-pyridin-4-ylmethyl-amine.
Yield : 72 %
1H NMR (300 MHz, CDCl3) δ 8.57 (dd, 2H), δ 7.47 (d, J=1.83 Hz, 1H), δ 7.42 (d, J=8.0 Hz, 1H), δ 7.29 (dd, 2H), δ 7.20 (dd, J=8.0 and 1.83 Hz, 1H), δ 3.81 (s, 2H), δ 3.76 (s, 2H), δ 1.75 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.612 g (5.714 mmol) of benzylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow liquid of benzyl-(3,4-dichloro-benzyl)-amine.
Yield : 89.1 %
1H NMR (300 MHz, CDCl3) δ 7.47 (d, J=2.2 Hz, 1H), δ 8.74 (d, J=8.0 Hz, 1H), δ 8.73 (m, 5H), δ 7.20 (dd, J=8.0 and 1.8 Hz, 1H), δ 3.79 (s, 2H), δ 3.76 (s, 2H), δ 1.60 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.698 g (5.714 mmol) of 4-(2-Aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-(2-pyridin-4-yl-ethyl)-amine.
Yield : 76.7 %
1H NMR (300 MHz, CDCl3) δ 8.53 (d, 2H), δ 7.39 (m, 2H), δ 7.15 (m, 3H), δ 3.76 (s, 2H), δ 2.91 (m, 2H), δ 2.83 (m, 2H), δ 2.37 (b, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.698 g (5.714 mmol) of 3-(2-Aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-(2-pyridin-3-yl-ethyl)-amine.
Yield: 62.24 %
1H NMR (300 MHz, CDCl3) δ 8.48 (s, 2H), δ 7.54 (dt, 1H), δ 7.39 (m, 2H), δ 7.26 (m, 1H), δ 7.13 (dd, J=8.4 and 2.1 Hz, 1H), δ 3.76 (s, 2H), δ 2.90 (m, 4H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.698 g (5.714 mmol) of 2-(2-aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate, n-hexane, and methanol as a mobile phase, to thereby obtain a dark-yellow liquid of (3,4-Dichloro-benzyl)-(2-pyridin-2-yl-ethyl)-amine.
Yield : 37.3 %
1H NMR (300 MHz, CDCl3) δ 8.55 (d, 1H), δ 7.64 (td, J=7.6 and 1.8 Hz, 1H), δ 7.41 (d, J=1.8 Hz 1H), δ 7.37 (d, J=8.0 Hz, 1H), δ 7.18 (m, 3H), δ 3.78 (s, 2H), δ 3.01 (m, 4H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.486 g (5.714 mmol) of cyclopentylamine was added thereto and reacted at room temperature for 1 hour. Then, 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow liquid of cyclopentyl-(3,4-dichloro-benzyl)-amine.
Yield : 96 %
1H NMR (300 MHz, CDCl3) δ 7.44 (d, J=1.8 Hz, 1H), δ 7.39 (d, J=8.0 Hz, 1H), δ 7.17 (dd, J=8.0 and 1.8 Hz, 1H), δ 3.72 (s, 2H), δ 3.12 (m, J=6.5 Hz, 1H), δ 1.87 (m, 8H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.692 g (5.714 mmol) of 2-phenylethylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of (3,4-Dichloro-benzyl)-phenethyl-amine.
Yield : 87.4 %
1H NMR (300 MHz, CDCl3) δ 7.38 (m, 7H), δ 7.12 (dd, J=8.4 and 1.8 Hz, 1H), δ 3.74 (s, 2H), δ 2.89 (m, 4H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.566 g (5.714 mmol) of cyclohexylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a yellow liquid of cyclohexyl-(3,4-dichloro-benzyl)-amine.
Yield : 70.2 %
1H NMR (300 MHz, CDCl3) δ 7.44 (d, J=1.8 Hz, 1H), δ 7.38 (d, J=8.0 Hz, 1H), δ 7.17 (dd, J=8.0 and 1.8 Hz, 1H), δ 3.76 (s, 2H), δ 2.47 (m, 1H), δ 1.91 (m, 10H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.646 g (5.714 mmol) of cycloheptylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a liquid of cycloheptyl-(3,4-dichlorobenzyl)-amine.
Yield : 64 %
1H NMR (300 MHz, CDCl3) δ 7.44 (d, J=1.8 Hz, 1H), δ 7.38 (d, J=8.4 Hz, 1H), δ 7.17 (dd, J=8.4 and 1.8 Hz, 1H), δ 3.76 (s, 2H), δ 2.47 (m, 1H), δ 1.91 (m, 12H) - After 1 g (9.423 mmol) of benzaldehyde was dissolved in 10 mL of methanol, 1.151 g (9.423 mmol) of 2-(2-aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-red liquid of benzyl-(2-pyridin-2-yl-ethyl)-amine.
Yield : 87 %
1H NMR (300 MHz, CDCl3) δ 8.53 (d, 1H), δ 7.61 (td, J=7.6 and 1.8 Hz, 1H), δ 7.31 (m, 7H), δ 3.83 (s, 2H), δ 3.08 (m, 4H) - After 1 g (8.189 mmol) of salicylaldehyde was dissolved in 10 mL of methanol, 1.000 g (8.189 mmol) of 2-(2-Aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.46 g (12.28 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of 2-[(2-Pyridin-2-yl-ethylamino)-methyl]-phenol.
Yield : 52.5 %
1H NMR (300 MHz, CDCl3) δ 8.53 (d, 1H), δ 7.64 (td, J=7.7 and 1.8 Hz, 1H), δ 7.17 (m, 3H), δ 7.00 (d, 1H), δ 6.82 (m, 2H), δ 4.01 (s, 2H), δ 3.13 (m, 4H) - After 1 g (5.405 mmol) of 2-Bromobenzaldehyde was dissolved in 10 mL of methanol, 0.660 g (5.405 mmol) of 2-(2-Aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.30 g (8.10 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-red liquid of (2-Bromo-benzyl)-(2-pyridin-2-yl-ethyl)-amine.
Yield: 31.8 %
1H NMR (300 MHz, CDCl3) δ 8.54 (m, 1H), δ 7.62 (td, J=7.6 and 1.8 Hz, 1H), δ 7.53 (dd, J=8.0 and 1.1 Hz, 1H), δ 7.38 (dd, J=7.6 and 1.8 Hz, 1H), δ 7.29 (td, 1H), δ 7.1 (d, J=7.6 Hz, 1H), δ 7.14 (m, 2H), δ 3.90 (s, 2H), δ 3.07 (m, 4H), δ 2.08 (b, 1H) - After 1 g (5.405 mmol) of 3-bromobenzaldehyde was dissolved in 10 mL of methanol, 0.660 g (5.405 mmol) of 2-(2-aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.30 g (8.10 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow liquid of (3-Bromo-benzyl)-(2-pyridin-2-yl-ethyl)-amine.
Yield : 40.5 %
1H NMR (300 MHz, CDCl3) δ 8.54 (d, J=4.3 Hz, 1H), δ 7.63 (td, J=7.7 and 1.8 Hz, 1H), δ 7.46 (s, 1H), δ 7.37 (d, J=7.7 Hz, 1H), δ 7.23 (m, 4H), δ 3.79 (s, 2H), δ 3.06 (m, 4H) - After 1 g (5.405 mmol) of 4-bromobenzaldehyde was dissolved in 10 mL of methanol, 0.660 g (5.405 mmol) of 2-(2-aminoethyl)pyridine was added thereto and reacted at room temperature for 1 hour. 0.30 g (8.10 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-red liquid of (4-Bromo-benzyl)-(2-pyridin-2-yl-ethyl)-amine.
Yield : 68.3 %
1H NMR (300 MHz, CDCl3) δ 8.53 (d, J=4.7 Hz, 1H), δ 7.62 (td, J=7.7 and 1.8 Hz, 1H), δ 7.43 (d, 2H), δ 7.19 (m, 4H), δ 3.78 (s, 2H), δ 3.06 (m, 4H) - After 1 g (9.423 mmol) of benzaldehyde was dissolved in 10 mL of methanol, 1.066 g (9.423 mmol) of cycloheptylamine was added thereto and reacted at room temperature for 1 hour. 0.53 g (14.13 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a pale-yellow liquid of benzyl-cycloheptyl-amine.
Yield : 73.2 %
1H NMR (300 MHz, CDCl3) δ 7.37 (m, 5H), δ 3.77 (s, 2H), δ 2.69 (m, 1H), δ 1.89 (m, 12H) - After 1 g (9.423 mmol) of benzaldehyde was dissolved in 10 mL of methanol, 0.934 g (9.423 mmol) of cyclohexylamine was added thereto and reacted at room temperature for 1 hour. 0.53 g (14.13 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of benzyl-cyclohexyl-amine.
Yield: 61.8 %
1H NMR (300 MHz, CDCl3) δ 7.32 (m, 5H), δ 3.77 (s, 2H), δ 3.16 (m, 1H), δ 1.90 (m, 10H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.761 g (5.714 mmol) of 1-aminoindan was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a white liquid of (3,4-dichloro-benzyl)-indan-1-yl-amine.
Yield: 61.2 %
1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=1.8 Hz, 1H), δ 7.39 (m, 2H), δ 7.25 (m, 4H), δ 4.28 (t, J=6.5 Hz, 1H), δ 3.91 (m, 2H), δ 3.00 (m, 1H), δ 2.87 (m, 1H), δ 2.46 (m, 1H), δ 1.87 (m, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.406 g (5.714 mmol) of cyclobuthylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of cyclobutyl-(3,4-dichloro-benzyl)-amine.
Yield : 45.7 %
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=2.19 Hz, 1H), δ 7.38 (d, J=8.4 Hz, 1H), δ 7.16 (dd, J= 8.4 and 2.19 Hz, 1H), δ 3.65 (s, 2H), δ 3.30 (m, 1H), δ 2.25 (m, 2H), δ 1.73 (m, 4H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.727 g (5.714 mmol) of cyclooctylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of cyclooctyl-(3,4-dichloro-benzyl)-amine.
Yield : 73.5 %
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=1.8 Hz, 1H), δ 7.38 (d, J=8.0 Hz, 1H), δ 7.17 (dd, J=8.0 and 1.8 Hz, 1H), δ 3.72 (s, 2H), δ 2.70 (m, 1H), δ 1.80 (m, 14H) - After 1 g (3.457 mmol) of N'-(3,4-dichlorobenzyl)-N,N-diethyl-propane-1,3-diamine was dissolved in 20 mL of methylene chloride, hydrogen chloride (7 mmol) was added thereto and stirred for 10 minutes. When a solid was formed, the resulting product was filtered to thereby obtain a salt of N'-(3,4-dichlorobenzyl)-N,N-diethyl-propane-1,3-diamine· 2HCl (i.e., a salt of Compound 1).
Yield : 100%
1H NMR (300 MHz, DMSO-d6) δ 10.72 (b, 1H), δ 9.86 (b, 2H), δ 7.97 (d, J=1.47 Hz 1H), δ 7.72 (d, J=8.07 Hz 1H), δ 7.63 (dd, J=8.07 and 1.47 Hz 1H), δ 4.15 (s, 2H), δ 3.15 (m, 8H), δ 2.18 (m, 2H), δ 1.24 (t, J=6.96 Hz, 6H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.984 g (5.714 mmol) of N,N-dibutylethylenediamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid N,N-dibutyl-N'-(3,4-dichlorobenzyl)ethane-1,2-diamine.
Yield : 86.3%
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=1.83 Hz, 1H), δ 7.39 (d, J=8.04 Hz, 1H), δ 7.17 (dd, J=1.83 and 8.04 Hz, 1H), δ 3.74 (s, 2H), δ 2.62 (m, 4H), δ 2.38 (t, J=6.96 Hz, 4H), δ 1.46 (m, 8H), δ 0.92 (t, J=6.96 Hz, 6H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 1.064 g (5.714 mmol) of 3-(dibutylamino)propylamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of N,N-dibutyl-N'-(3,4-dichlorobenzyl)propane-1,3-diamine.
Yield : 70.4%
1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=1.83 Hz, 1H), δ 7.38 (d, J=8.07 Hz, 1H), δ 7.17 (dd, J=1.83 and 8.07 Hz, 1H), δ 3.72 (s, 2H), δ 6.65 (t, J=6.6 Hz, 2H), δ 2.46 (m, 6H), δ 1.69 (m, 2H), δ 1.45 (m, 10H), δ 0.93 (t, J=7.32 Hz, 1H) - After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.926 g (5.714 mmol) of N-(3-aminopropyl)diethanolamine was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a colorless liquid of 2-[[3-(3,4-Dichlorobenzylamino)propyl]-(2-hydroxyethyl)amino]ethanol.
Yield: 64.1 %
1H NMR (300 MHz, CDCl3) δ 7.42 (m, 2H), δ 7.19 (dd, J=2.19 and 8.43 Hz, 1H), δ 3.71 (s, 2H), δ 3.63 (t, J=5.13, 4H), δ 2.73 (m, 8H), δ 1.70 (m, 2H) - To investigate whether
Compounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 had an microalgae-killing effect, flagellates of the species Chattonella Marina, the species Heterosigma circularisquama, the species Cochlodinium Polykrikoides, and the species Heterosigma akashiwo, and blue-green algae of the genus Microcystis were treated withCompounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51. After the treatment, microalgae-destroying effects ofCompounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 were analyzed by measuring the half-maximal inhibitory concentration (IC50), which represents the concentration of each compound that is required for 50% inhibition of a total microalgae cell count. -
- In
Equation 1, Y represents an algicidal activity (%) at an inoculation concentration of each compound, A and D represent a maximum algicidal activity (%) and a minimum algicidal activity (%), respectively, at an inoculation concentration of each compound, C represents an IC50 value within an inoculation concentration range, and B represents Hillslope (i.e., a slope of the four-parameter logistic curve which will be described below). -
- In
Equation 2, T (treatment group) and C (control group) represent algae densities in cell counts when each compound was inoculated and was not inoculated, respectively, and t represents the number of days which had passed after the inoculation. - First, the above-listed microalgae were cultured in a culture flask at a temperature of about 20°C under light conditions, and a medium used was Guillard's f/2 medium which is commonly used in the art (Guillard RRL and Keller MD. Culturing dinoflagellates. In: Spector (Ed.), Dinoflagellates. New York: Academic Press; 1984, 391442).
- After the cultured microalgae were transferred onto a 24-well plate, Chattonella Marina, Heterosigma circularisquama, Cochlodinium Polykrikoides, and Heterosigma akashiwo, which were in an exponential growth phase, were treated with
Compounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 47 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 47 at concentrations of 0.1 uM, 0.2 uM, 0.5 uM, 1 uM, 2 uM, and 5 uM, and then cultured for 1 day. - Microcystis aeruginosa was treated with
Compounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 at concentrations of 0.1 uM, 0.2 uM, 0.5 uM, 1 uM, 2 uM, 5 uM, 10 uM, 15 uM, and 20 uM and then cultured for 5 days. - Control groups were not treated with any of the compounds synthesized in the above-identified examples. After incubation, the number of cells of each alga was counted using a Burker-Tukr hemocytometer, and IC50 values were calculated according to
Equation 1 using SigmaPlot Version 11.2 software (Standard curve: the four-parameter logistic curve). The results are shown in Tables 1 and 2.[Table 1] Compound Chattonella Marina Heterocapsa Circularisquama Cochlodinium Polykrikoides Heterosigma Akashiwo Microcystis aeruginosa 3,4-dichlorobenzylamines Example 1 1 2.9 1.76 2.3 1.58 4.89 Example 2 2 2.6 3.4 0.327 1.3 0.57 Example 3 3 >5 3.1 >5 2.25 8.41 Example 5 5 >5 >5 >5 1.3 14.17 Example 6 6 >5 4.8 4.417 1.3 8.64 Example 7 7 2 1.5 1.53 0.28 11.61 Example 8 8 0.81 3.3 0.29 1.26 0.09 Example 17 17 >5 >5 >5 1.18 >20 Example 18 18 2.67 >5 4.38 0.73 11.83 Example 19 19 3.5 >5 4.14 1.27 13.8 Example 20 20 3.16 2.86 3.516 0.44 >20 Example 21 21 >5 3.3 3.6 1.28 9.66 Example 23 23 >5 >5 >5 1.54 11.07 Example 25 25 >5 2.83 4 1.19 11.11 Example 26 26 3.4 >5 >5 0.72 >20 Example 27 27 >5 3.55 2 0.79 >20 Example 28 28 >5 >5 >5 2.28 15.24 Example 29 29 3.46 3.23 2.75 0.6 14.38 Example 30 30 3.47 1.91 2.7 0.42 >20 Example 31 31 3.5 1.6 0.424 0.59 >20 Example 32 32 0.31 1.05 0.5 0.18 19.58 Example 33 33 0.32 1.04 0.36 0.243 19.47 Example 34 34 0.46 1.5 0.875 0.12 5.97 Example 35 35 0.29 1.14 0.15 0.218 14.59 Example 36 36 0.25 0.69 0.15 0.263 3.09 Example 45 45 1.44 2 0.31 1.14 >20 Example 46 46 1.13 3.08 1.667 0.482 15.79 Example 47 47 0.5 1.19 0.1 0.34 14.97 Example 48 48 - - - - 0.78 Example 49 49 - - - - 0.88 Example 50 50 - - - - 0.54 Example 51 51 - - - - 2.27 [Table 2] Compound Chattonella Marina Heterocapsa Circulariaquama Cochlodinium Polykrikoides Heterosigma Akashiwo Microcystis aeruginosa 3,4-dichlorobenzamides Example 9 9 >5 1.97 4.55 1.85 0.97 Example 10 10 >5 >5 >5 1.63 >5 Example 12 12 >5 >5 >5 1.55 >5 Example 13 13 4.5 5 2.22 2.27 >5 Benzylamines Example 37 37 0.34 >5 >5 0.13 >5 Example 42 42 0.52 >5 >5 0.15 >5 Example 43 43 >5 >5 >5 0.67 >5 2-hydroxybenzylamines Example 38 38 0.91 >5 >5 0.13 >5 n-bromobenzylamines Example 39 39 1.12 >5 >5 0.28 >5 Example 40 40 0.74 >5 3.5 0.57 >5 Example 41 41 0.72 >5 >5 0.14 >5 Phenyl propenones Example 22 22 >5 >5 1.66 3.67 >5 Example 24 24 >5 >5 1.33 1.7 >5 - Referring to Tables 1 and 2,
Compounds 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 synthesized in Examples 1 to 3, 5 to 10, 12, 13, 17 to 43, and 45 to 51 were found to have an algicidal effect on at least one of Chattonella Marina, Heterosigma circularisquama, Cochlodinium Polykrikoides, Heterosigma akashiwo, and Microcystis aeruginosa. - For reference, a IC50 value greater than 5 means nearly zero microalgae-filling effect.
- To investigate a microalgae-destroying effect of
Compound 35 synthesized in Example 35, culture solutions of Chattonella Marina, Heterosigma Circularisquama, Cochlodinium Polykrikoides, and Heterosigma akashiwo (40 mL, initial population number: about 15X104 to 18X104 /mL) were each treated with a solution of Compound 35 (1 µM in dimethyl sulfoxide (DMSO) and f/2 medium) for about 6 hours. A microalgae culture solution not treated with a solution ofCompound 35 was used as a control group. After the treatment, viable cell ratios of the microalgae with respect to time were measured, and it was also observed whether the microalgae were destroyed. The results are shown inFIGS. 1 and2 . - Referring to
FIG. 1 , the viable cell ratios of the microalgae were found to have decreased with time, indicating thatCompound 35 had a high algicidal effect on the four kinds of the microalgae. -
FIG. 2 shows microscope images of the four microalgal species observed after the treatment withCompound 35, wherein (a), (b), (c), and (d) represent microscope images of Cochlodinium Polykrikoides, Heterosigma akashiwo, Heterosigma circularisquama, and Chattonella Marina, respectively, and (a)-1, (a)-3, (b)-1, (c)-1, and (d)-1 represent control groups not treated withCompound 35. - Referring to
FIG. 2 , the four microalgal species treated withCompound 35 were found to have been destroyed, as shown in (a)-2, (a)-4, (b)-2, (b)-3, (c)-2, (c)-3, (d)-2, and (d)-3 ofFIG. 2 . - To investigate a microalgae-destroying effect of
Compound 2 synthesized in Example 2, culture solutions of Microcystis aeruginosa (40 mL; initial population number: 100X104 /mL) in DMSO and BG11 medium were each treated with solutions ofCompound 2 at 0.5 µM, 1 µM, and 2 µM and observed for 2 days. A culture solution of the microalgae not treated with a solution ofCompound 2 was used as a control group. The results are shown inFIG. 3 - Referring to
FIG. 3 ,Compound 2 was found to have a high algicidal effect on the Microcystis. - An acute toxicity test was performed on Daphnia magna (water flea) using
Compounds Compounds FIG. 4 . - Referring to
FIG. 4 , when treated with the solutions ofCompounds Compounds - An acute toxicity test on Danio rerio (zebrafish) was performed using
compounds 33and 35 synthesized inExamples 33and 35. In particular, 2-cm-sized Danio rerio, which had been 3 months since hatching, was acclimatized for 14 days before the start of the experiment. The Danio rerio were feed twice a day during the acclimation period. Next, solutions ofCompounds Compounds FIG. 5 . - Referring to
FIG. 5 , when treated with the solutions ofCompounds Compounds - While one or more embodiments have been described with reference to the appended drawings, it should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation and that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims. Therefore, the scope of the disclosure is defined not by the detailed description of the disclosure but by the appended claims and equivalents thereof.
Claims (26)
- A composition for destroying microalgae or mosses, the composition comprising a compound represented by one of Formulae 1 to 3 or a salt thereof as an active ingredient:
A1 to A3 are each independently selected from hydrogen, deuterium, -N(R11)(R12), a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group,
R1 to R3, R11, and R12 are each independently selected from hydrogen, deuterium, -F, -CI, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, and a substituted or unsubstituted C1-C10 alkoxy group,
b1 to b3 are each independently an integer of 0 to 5, wherein at least two R1s are the same as or different from each other when b1 is 2 or greater, at least two R2s are the same as or different from each other when b2 is 2 or greater, and at least two R3s are the same as or different from each other when b3 is 2 or greater,
n1 to n3 are each independently an integer of 0 to 10, and
at least one substituent of the substituted C1-C10 alkyl group, the substituted C2-C10 alkenyl group, the substituted C2-C10 alkynyl group, the substituted C1-C10 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, and the substituted C1-C60 heteroaryl group is selected from deuterium, -F, -CI, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, and a C1-C10 alkyl group. - The composition of claim 1, wherein, in Formulae 1 to 3, A1 to A3 are each independently selected from -N(R11)(R12), a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C10 aryl group, and a substituted or unsubstituted C1-C10 heteroaryl group.
- The composition of claim 1, wherein, in Formulae 1 to 3, A1 to A3 are each independently selected from groups represented by Formulae 4-1 to 4-16:
R11 to R14 and R21 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, and a substituted or unsubstituted C1-C10 alkyl group,
b11 is an integer of 0 to 2,
b12 is an integer of 0 to 3,
b13 is an integer of 0 to 4,
b14 is an integer of 0 to 5,
b15 is an integer of 0 to 6,
b16 is an integer of 0 to 7, and
* is a binding site to a neighboring atom. - The composition of claim 3, wherein, in Formulae 4-1 to 4-16, R11 to R14 are each independently selected from
a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group; and
a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each substituted with a -OH group, and
R21 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and -OH. - The composition of claim 3, wherein, in Formulae 4-1 to 4-16, b11 to b16 are each independently 0 or 1.
- The composition of claim 1, wherein, in Formulae 1 to 3, R1 to R3 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, a cyano group, a nitro group, an amino group, an amidino group, and a substituted or unsubstituted C1-C10 alkyl group.
- The composition of claim 1, wherein, in Formulae 1 to 3, R1 to R3 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and -OH.
- The composition of claim 1, wherein, in Formulae 1 to 3, b1 to b3 are each independently 0, 1, or 2.
- The composition of claim 1, wherein, in Formulae 1 to 3, R1 to R3 are -Br or -OH when b1 to b3 are each 1; and
R1 to R3 are each -Cl when b1 to b3 are each 2. - The composition of claim 1, wherein, in Formulae 1 to 3, two R1s, two R2s, and two R3s are in a para position when b1 to b3 are each 2.
- The composition of claim 1, wherein n1 to n3 are each independently an integer of 0 to 3.
- The composition of claim 1, wherein the composition comprises at least one of compounds represented by Formulae 1-1 to 1-6, 2-1 to 2-6, and 3-1 to 3-6 or a salt thereof as an active ingredient:
- The composition of claim 13, wherein, in Formulae 1-1 to 1-6, 2-1 to 2-6, and 3-1 to 3-6,
A1 to A3 are each independently selected from groups represented by Formulae 5-1 to 5-23, and
n1 to n3 are each independently an integer of 0 to 3: - The composition of claim 1, wherein the microalgae are selected from blue-green algae, diatoms, green algae, euglenoid algae, flagellates, yellow-green algae, Dinophyta, raphidophytes, and algae with a biodiesel-producing ability.
- The composition of claim 1, wherein the mosses are selected from the class Takakiopsida, the class Sphagnopsida, the class Andreaeopsida, the class Andreaeobryopsida, the class Oedipodiopsida, the class Polytrichopsida, the class Tetraphidopsida, and the class Bryopsida.
- The composition of claim 16, wherein the blue-green algae are selected from the genus Microcystis, the genus Anabaena, the genus Aphanizomenon, and the genus Oscillatoria.
- The composition of claim 16, wherein the diatoms are selected the genus Synedra, the genus Asterionella, the genus Cyclotella, the genus Melosira, the genus Skeletonema costatum, the genus Chaetoceros, the genus Thalassiosira, the genus Leptocylindrus, the genus Nitzschia, the genus Cylindrotheca, the genus Eucampia, and the genus Odontella.
- The composition of claim 16, wherein the green algae are selected from the genus Closterium, the genus Pediastrum, and the genus Scenedesmus.
- The composition of claim 16, wherein the euglenoid algae are of the genus Trachelomonas or the genus Euglena.
- The composition of claim 16, wherein the flagellates are selected from the genus Peridinium, the genus Heterosigma, the genus Heterocapsa, the genus Cochlodinium, the genus Prorocentrum, the genus Ceratium, the genus Noctiluca, the genus Scrippsiella, the genus dinophysis, the genus Alexandrium, the genus Eutreptiella, the genus Pfiesteria, the genus Chattonella, the genus Emiliania, and the genus Gymnodinium.
- The composition of claim 16, wherein the yellow-green algae are of the genus Uroglena.
- The composition of claim 16, wherein the Dinophyta and the raphidophytes are selected from the genus Heterosigma, the genus Heterocapsa, the genus Cochlodinium, the genus Prorocentrum, the genus Ceratium, the genus Noctiluca, the genus Scrippsiella, the genus dinophysis, the genus Alexandrium, the genus Eutreptiella, the genus Pfiesteria, the genus Chattonella, the genus Emiliania, and the genus Gymnodinium.
- The composition of claim 16, wherein the algae with a biodiesel-producing ability is selected the genus Pseudochoricystis, the genus Botryococcus, and the genus Dunaliella.
- A method of destroying microalgae or mosses, the method comprising treating a moss cultivation facility, a marine microalgae cultivation facility, an area in which green or red tide is occurring, or an area in which green or red tide is expected to occur with the composition of claim 1 for destroying microalgae or mosses.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20150143373 | 2015-10-14 | ||
KR1020160044946A KR101819190B1 (en) | 2015-10-14 | 2016-04-12 | Composition for destructing microalgae |
PCT/KR2016/009070 WO2017065401A1 (en) | 2015-10-14 | 2016-08-18 | Composition for destruction of microalgae or sphaerocarpus |
Publications (3)
Publication Number | Publication Date |
---|---|
EP3363288A1 true EP3363288A1 (en) | 2018-08-22 |
EP3363288A4 EP3363288A4 (en) | 2019-07-03 |
EP3363288B1 EP3363288B1 (en) | 2022-09-07 |
Family
ID=58704375
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP16855619.9A Active EP3363288B1 (en) | 2015-10-14 | 2016-08-18 | Composition for destruction of microalgae or mosses |
Country Status (7)
Country | Link |
---|---|
US (1) | US11044909B2 (en) |
EP (1) | EP3363288B1 (en) |
JP (1) | JP6732917B2 (en) |
KR (1) | KR101819190B1 (en) |
CN (1) | CN108347925B (en) |
BR (1) | BR112018007330B1 (en) |
PH (1) | PH12018500655A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113994946A (en) * | 2021-10-12 | 2022-02-01 | 广东海洋大学 | Application of o-hydroxy cinnamic acid in removing harmful benthic diatom |
CN115557601A (en) * | 2022-11-08 | 2023-01-03 | 成都理工大学 | Biomass microsphere, preparation method and application thereof, bioreactor and underground well |
CN116904318B (en) * | 2023-08-04 | 2024-02-06 | 江苏海洋大学 | Method for stably proliferating noctilucent algae based on mixed culture |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB518453A (en) * | 1937-10-01 | 1940-02-27 | Monsanto Chemicals | Insecticides |
US3775313A (en) * | 1971-03-19 | 1973-11-27 | Millmaster Onyx Corp | Biocidal treatment of water using 2,4,5-trichloroaniline derivatives |
US3871861A (en) * | 1971-04-02 | 1975-03-18 | Millmaster Onyx Corp | Method of inhibiting algae utilizing trimethylbenzylaminoethylamine |
JPS5290630A (en) * | 1976-01-21 | 1977-07-30 | Sumitomo Chem Co Ltd | Algicide |
ZA793568B (en) * | 1978-07-26 | 1981-02-25 | Duphar Int Res | Algicidal composition |
JPH06247804A (en) * | 1993-02-22 | 1994-09-06 | Mitsubishi Gas Chem Co Inc | Antifouling agent for aquatic organism |
EP0880893A1 (en) * | 1997-05-29 | 1998-12-02 | Rohm And Haas Company | Method for controlling algae |
EP1059033A4 (en) * | 1998-02-25 | 2002-03-20 | Nissan Chemical Ind Ltd | Industrial antibacterial/antifungal agents, algicides and anti-biological adhesion agents containing benzylamines |
JP2995472B1 (en) * | 1998-12-04 | 1999-12-27 | 伯東株式会社 | Algae killing methods in water systems |
MXPA03001972A (en) | 2000-10-16 | 2004-09-10 | Shangai Inst Of Organic Chemis | New 2-pyrimidinyloxy-n-aryl-benzylamine derivatives, their processes and uses. |
CN1147479C (en) * | 2001-04-20 | 2004-04-28 | 中国科学院上海有机化学研究所 | 2-pyrimidyloxybenzyl substituted naphthyl amine derivative and its synthesis and use |
US7572818B2 (en) | 2002-08-12 | 2009-08-11 | Bayer Cropscience S.A. | 2-pyridylethylbenzamide derivative |
EP3008998A1 (en) * | 2004-02-11 | 2016-04-20 | Fmc Corporation | Method for control of algae, mosses, liverworts, hornworts and bryophytes |
MX2010005061A (en) * | 2007-11-10 | 2010-09-09 | Joule Unltd Inc | Hyperphotosynthetic organisms. |
EP3670524A1 (en) * | 2008-09-24 | 2020-06-24 | Tel HaShomer Medical Research Infrastructure and Services Ltd. | Peptides and compositions for prevention of cell adhesion and methods of using same |
WO2010090458A2 (en) | 2009-02-04 | 2010-08-12 | 조선대학교산학협력단 | Composition for controlling harmful algae |
JP2011068741A (en) * | 2009-09-25 | 2011-04-07 | Nippon Shokubai Co Ltd | Method for extracting oil-and-fat from scenedesmus algae, and application of oil-and-fat and degreaded residue |
JP5523411B2 (en) * | 2010-08-24 | 2014-06-18 | インダストリー−アカデミック コーオペレイション ファウンデーション, チョソン ユニヴァーシティー | Control method of harmful algae using bionanocapsid |
CN102007911B (en) * | 2010-11-25 | 2013-09-25 | 中化蓝天集团有限公司 | Active composition for cotton field weeding and phytocide thereof |
KR101436792B1 (en) * | 2011-07-08 | 2014-09-05 | 한양대학교 산학협력단 | A Composition containing Naphthoquinone for Controlling Harmful Algae |
JP2014051480A (en) * | 2012-09-10 | 2014-03-20 | Japan Enviro Chemicals Ltd | Chalcone compound or salt thereof, and bactericidal composition for industrial use |
MX2015003660A (en) | 2012-09-21 | 2015-06-05 | Abbott Lab | Nutritional compositions including calcium beta-hydroxy-beta-meth ylbutyrate, protein and low levels of electrolytes. |
KR101761848B1 (en) * | 2013-02-22 | 2017-07-26 | 조선대학교산학협력단 | Composition for Distructing Microalgae |
WO2015089288A1 (en) * | 2013-12-11 | 2015-06-18 | Arch Chemicals, Inc. | Method of controlling algae in a body of water |
-
2016
- 2016-04-12 KR KR1020160044946A patent/KR101819190B1/en active IP Right Grant
- 2016-08-18 US US15/762,368 patent/US11044909B2/en active Active
- 2016-08-18 BR BR112018007330-0A patent/BR112018007330B1/en active IP Right Grant
- 2016-08-18 CN CN201680059534.9A patent/CN108347925B/en active Active
- 2016-08-18 EP EP16855619.9A patent/EP3363288B1/en active Active
- 2016-08-18 JP JP2018534449A patent/JP6732917B2/en active Active
-
2018
- 2018-03-23 PH PH12018500655A patent/PH12018500655A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
PH12018500655A1 (en) | 2018-10-01 |
CN108347925B (en) | 2021-07-16 |
CN108347925A (en) | 2018-07-31 |
KR20170043989A (en) | 2017-04-24 |
KR101819190B1 (en) | 2018-01-16 |
EP3363288A4 (en) | 2019-07-03 |
US11044909B2 (en) | 2021-06-29 |
JP6732917B2 (en) | 2020-07-29 |
BR112018007330B1 (en) | 2022-10-04 |
KR101819190B9 (en) | 2023-12-15 |
EP3363288B1 (en) | 2022-09-07 |
JP2018531992A (en) | 2018-11-01 |
US20180271091A1 (en) | 2018-09-27 |
BR112018007330A2 (en) | 2018-10-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3363288B1 (en) | Composition for destruction of microalgae or mosses | |
CN103749463A (en) | Methods of controlling algae with Thaxtomin and Thaxtomin compositions | |
DE60223194T2 (en) | Quaternary ammonium salts with a tertiary alkyl group | |
WO2018223633A1 (en) | Application of tetrahydrobenzazole in preparation of agricultural fungicide or fungicide composition and preparation method therefor | |
KR101761848B1 (en) | Composition for Distructing Microalgae | |
KR101829962B1 (en) | A Composition for controlling harmful algae comprising naphthoquinone derivatives and method for controlling harmful using the same | |
IE48789B1 (en) | Algicidal composition and method of preventing or controlling algae with said composition | |
US20220144752A1 (en) | Water-soluble naphthoquinone derivative composition and method for producing same, water-soluble composition for controlling harmful algae, method for controlling large-scale harmful algae, and automation system for ai-monitoring, removing, and preventing large-scale harmful algae | |
CN104761542A (en) | Indazolyl-containing amide compound and application thereof | |
Elgellal et al. | Preparation characterization and biological evaluation of Schiff-Base of some drug substances | |
KR20180097494A (en) | Cosmetic ingcluding Adhesive Diatoms extract and manufacutring method thereof | |
KR20130006381A (en) | A composition containing naphthoquinone for controlling harmful algae | |
Abd El-Hady et al. | Phytoplankton biochemical contents and zooplankton composition in vegetated and non-vegetated regions in Bardawil Lagoon, North Sinai, Egypt | |
Jo et al. | Novel rhodanine derivatives are selective algicides against Microcystis aeruginosa | |
US20210371674A1 (en) | Method of treatment of a surface | |
KR101782618B1 (en) | Composition for Distructing Microalgae | |
CN109608392A (en) | Stilbene class similar compound and its preparation method and application | |
Pandurangan et al. | Cultivation of spirulina platensis having humic acid as substrate for soap production | |
Okatani et al. | Induction and promotion of flowering by heat-treated catecholamines in Lemna paucicostata | |
CN115160207B (en) | Benzoyl thiourea compound, preparation method thereof and application of red tide algae algicide | |
CN108684665B (en) | Application of compound 3,3 ', 5,5 ' -tetrabromo-2, 2 ' -biphenol in inhibiting and removing algae | |
KR20010041333A (en) | Industrial antibacterial/antifungal agents, algicides and anti-biological adhesion agents containing benzylamines | |
US20140110350A1 (en) | Methods of inhibiting cyanobacteria growth by administering gramine derivatives | |
Zaml et al. | Synthesis, Characterization of New Metal Complexes of Ligand [3-(4-hydroxyphenyl)-2-(3-(4-methoxybenzoyl) thio ureido) propanoicacid](HMP) and Study of the Biological Activity | |
CN114195707A (en) | High-efficiency broad-spectrum plant antibacterial agent BZ |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20180403 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
RIC1 | Information provided on ipc code assigned before grant |
Ipc: C02F 1/50 20060101ALI20190225BHEP Ipc: A01N 35/04 20060101ALI20190225BHEP Ipc: A01N 31/00 20060101ALI20190225BHEP Ipc: A01N 43/40 20060101ALI20190225BHEP Ipc: A01N 33/04 20060101AFI20190225BHEP Ipc: A01N 33/06 20060101ALI20190225BHEP Ipc: A01N 37/18 20060101ALI20190225BHEP Ipc: A01N 33/08 20060101ALI20190225BHEP Ipc: C02F 1/40 20060101ALI20190225BHEP Ipc: A01N 35/06 20060101ALI20190225BHEP Ipc: A01N 37/10 20060101ALI20190225BHEP |
|
A4 | Supplementary search report drawn up and despatched |
Effective date: 20190605 |
|
RIC1 | Information provided on ipc code assigned before grant |
Ipc: A01N 33/04 20060101AFI20190529BHEP Ipc: A01N 31/00 20060101ALI20190529BHEP Ipc: A01N 37/10 20060101ALI20190529BHEP Ipc: A01N 33/08 20060101ALI20190529BHEP Ipc: A01N 35/06 20060101ALI20190529BHEP Ipc: C02F 1/40 20060101ALI20190529BHEP Ipc: A01N 37/18 20060101ALI20190529BHEP Ipc: A01N 33/06 20060101ALI20190529BHEP Ipc: C02F 1/50 20060101ALI20190529BHEP Ipc: A01N 35/04 20060101ALI20190529BHEP Ipc: A01N 43/40 20060101ALI20190529BHEP |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20200221 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: GRANT OF PATENT IS INTENDED |
|
INTG | Intention to grant announced |
Effective date: 20220406 |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE PATENT HAS BEEN GRANTED |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP Ref country code: AT Ref legal event code: REF Ref document number: 1516301 Country of ref document: AT Kind code of ref document: T Effective date: 20220915 |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602016074896 Country of ref document: DE |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG9D |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: MP Effective date: 20220907 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: RS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20221207 Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 1516301 Country of ref document: AT Kind code of ref document: T Effective date: 20220907 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20221208 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SM Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230109 Ref country code: ES Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230107 Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 602016074896 Country of ref document: DE |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 Ref country code: AL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
26N | No opposition filed |
Effective date: 20230608 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20230824 Year of fee payment: 8 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20230821 Year of fee payment: 8 Ref country code: DE Payment date: 20230824 Year of fee payment: 8 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: S13C Free format text: APPLICATION FILED; APPLICATION FOR A PERSON NOT TO BE MENTIONED AS INVENTOR UNDER SECTION 13(3) FILED ON 4 JANUARY BY CUREARTH, INC |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: S13C Free format text: APPLICATION DETERMINED; IN A DECISION OF THE COMPTROLLER DATED 21 FEBRUARY 2024, THE COMPTROLLER FOUND THAT HYUNG JOON CHA SHOULD NOT HAVE BEEN MENTIONED AS A JOINT INVENTOR IN THE PUBLISHED PATENT FOR THE INVENTION AND DIRECTED THAT AN ADDENDUM SLIP BE PREPARED TO REFLECT THIS. |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20220907 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230818 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230818 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230831 |
|
REG | Reference to a national code |
Ref country code: BE Ref legal event code: MM Effective date: 20230831 |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: MM4A |